Jump To Section:

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000207

Secondary Accession Numbers

HMDB0002066
HMDB00207
HMDB02066

Metabolite Identification

Common Name

Oleic acid

Description

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70%). Oleic acid triglycerides also make up 59-75% of pecan oil, 61% of canola oil, 36-67% of peanut oil, 60% of macadamia oil, 20-80% of sunflower oil, 15-20% of grape seed oil, sea buckthorn oil, 40% of sesame oil, and 14% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000207
     RDKit          3D
Oleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -6.3665    1.9995    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4256    0.5166    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7428   -0.2404   -0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2925    0.2245   -0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -0.4807   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.9541   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9184   -2.5399    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -2.3002    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537   -0.9265    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487   -0.2966   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -0.8351   -1.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189   -0.8113   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.6048   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.4962   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    1.8748   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845    1.8301    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987    0.9893    1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8894    1.0142    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6454    1.6466    0.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4842    0.3132    2.6314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1086    2.2561   -0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6034    2.4667    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3511    2.4509    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9304    0.3029    2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4836    0.1963    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888    0.0294   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512   -1.3023    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141    1.3011   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8113    0.1431    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -0.2718   -2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6016    0.0362   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858   -2.3672   -1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5904   -2.3038   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.6646    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -2.2706    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619   -2.9301    1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -2.8055   -0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   -0.3679    1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    0.7450    0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2642   -1.8180   -1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390   -0.1696   -2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189   -1.2104   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -1.3861    0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    1.2579   -1.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    1.0523    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262    0.0221   -1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410   -0.2171    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974    2.3092    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173    2.4692   -1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155    1.3969   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4157    2.8755    0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9504    1.3885    2.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0949   -0.0543    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6763   -0.6849    2.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END

  Mrv1652309272007412D          

 20 19  0  0  0  0            999 V2000
   -3.7393   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544   -0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1677   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8826   -0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5958   -0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8826    0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3102   -0.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965   -0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6574   -0.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669   -0.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8821   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859   -0.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5149   -0.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2300   -0.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9438   -0.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3718   -0.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  9 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 15  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000207

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

> <INCHI_KEY>
ZQPPMHVWECSIRJ-KTKRTIGZSA-N

> <FORMULA>
C18H34O2

> <MOLECULAR_WEIGHT>
282.4614

> <EXACT_MASS>
282.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.092366766057495

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z)-octadec-9-enoic acid

> <ALOGPS_LOGP>
7.68

> <JCHEM_LOGP>
6.783798451000001

> <ALOGPS_LOGS>
-6.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.4022

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000207
     RDKit          3D
Oleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -6.3665    1.9995    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4256    0.5166    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7428   -0.2404   -0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2925    0.2245   -0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -0.4807   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.9541   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9184   -2.5399    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -2.3002    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537   -0.9265    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487   -0.2966   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -0.8351   -1.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189   -0.8113   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.6048   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.4962   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    1.8748   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845    1.8301    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987    0.9893    1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8894    1.0142    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6454    1.6466    0.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4842    0.3132    2.6314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1086    2.2561   -0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6034    2.4667    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3511    2.4509    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9304    0.3029    2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4836    0.1963    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888    0.0294   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512   -1.3023    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141    1.3011   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8113    0.1431    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -0.2718   -2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6016    0.0362   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858   -2.3672   -1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5904   -2.3038   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.6646    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -2.2706    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619   -2.9301    1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -2.8055   -0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   -0.3679    1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    0.7450    0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2642   -1.8180   -1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390   -0.1696   -2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189   -1.2104   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -1.3861    0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    1.2579   -1.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    1.0523    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262    0.0221   -1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410   -0.2171    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974    2.3092    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173    2.4692   -1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155    1.3969   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4157    2.8755    0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9504    1.3885    2.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0949   -0.0543    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6763   -0.6849    2.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -6.980  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.315  -0.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.646  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.981  -0.386   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -12.312  -1.154   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0     -10.981   1.154   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.647  -0.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.312  -1.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.980  -0.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.227  -0.376   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.312  -0.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.647  -1.144   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.229  -1.144   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.894  -0.376   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.562  -1.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.561  -0.372   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.896  -1.139   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.228  -0.367   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.562  -1.133   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.894  -0.361   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   12                                                       
CONECT   10   11   15                                                       
CONECT   11   10   12                                                       
CONECT   12   11    9                                                       
CONECT   13   14   16                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0000207
HETATM    1  C1  UNL     1      -6.367   1.999   0.877  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.426   0.517   1.102  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.743  -0.240  -0.035  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.292   0.225  -0.065  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.535  -0.481  -1.172  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.510  -1.954  -1.028  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.918  -2.540   0.181  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.483  -2.300   0.482  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.054  -0.926   0.672  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.149  -0.297  -0.027  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.625  -0.835  -1.150  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.119  -0.811  -0.862  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.593   0.605  -0.612  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.101   0.496  -0.336  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.607   1.875  -0.084  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.085   1.830   0.187  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.399   0.989   1.390  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.889   1.014   1.579  1.00  0.00           C  
HETATM   19  O1  UNL     1       8.645   1.647   0.822  1.00  0.00           O  
HETATM   20  O2  UNL     1       8.484   0.313   2.631  1.00  0.00           O  
HETATM   21  H1  UNL     1      -6.109   2.256  -0.169  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.603   2.467   1.522  1.00  0.00           H  
HETATM   23  H3  UNL     1      -7.351   2.451   1.165  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.930   0.303   2.062  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.484   0.196   1.212  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.189   0.029  -1.014  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.851  -1.302   0.187  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.314   1.301  -0.340  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.811   0.143   0.914  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.154  -0.272  -2.110  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.602   0.036  -1.345  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.086  -2.367  -1.977  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.590  -2.304  -1.064  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.057  -3.665   0.099  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.549  -2.271   1.062  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.262  -2.930   1.429  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.825  -2.806  -0.258  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.547  -0.368   1.493  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.048   0.745   0.262  1.00  0.00           H  
HETATM   40  H20 UNL     1       0.264  -1.818  -1.447  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.439  -0.170  -2.058  1.00  0.00           H  
HETATM   42  H22 UNL     1       2.619  -1.210  -1.768  1.00  0.00           H  
HETATM   43  H23 UNL     1       2.331  -1.386   0.051  1.00  0.00           H  
HETATM   44  H24 UNL     1       2.442   1.258  -1.489  1.00  0.00           H  
HETATM   45  H25 UNL     1       2.065   1.052   0.251  1.00  0.00           H  
HETATM   46  H26 UNL     1       4.526   0.022  -1.239  1.00  0.00           H  
HETATM   47  H27 UNL     1       4.241  -0.217   0.494  1.00  0.00           H  
HETATM   48  H28 UNL     1       4.097   2.309   0.795  1.00  0.00           H  
HETATM   49  H29 UNL     1       4.417   2.469  -1.009  1.00  0.00           H  
HETATM   50  H30 UNL     1       6.615   1.397  -0.689  1.00  0.00           H  
HETATM   51  H31 UNL     1       6.416   2.876   0.358  1.00  0.00           H  
HETATM   52  H32 UNL     1       5.950   1.388   2.312  1.00  0.00           H  
HETATM   53  H33 UNL     1       6.095  -0.054   1.263  1.00  0.00           H  
HETATM   54  H34 UNL     1       8.676  -0.685   2.509  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   19   20
CONECT   20   54
END

HMDB0000207
     RDKit          3D
Oleic acid
 54 53  0  0  0  0  0  0  0  0999 V2000
   -6.3665    1.9995    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4256    0.5166    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7428   -0.2404   -0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2925    0.2245   -0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -0.4807   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.9541   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9184   -2.5399    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -2.3002    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537   -0.9265    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487   -0.2966   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6247   -0.8351   -1.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189   -0.8113   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.6048   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.4962   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    1.8748   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845    1.8301    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987    0.9893    1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8894    1.0142    1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6454    1.6466    0.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4842    0.3132    2.6314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1086    2.2561   -0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6034    2.4667    1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3511    2.4509    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9304    0.3029    2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4836    0.1963    1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1888    0.0294   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8512   -1.3023    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141    1.3011   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8113    0.1431    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -0.2718   -2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6016    0.0362   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858   -2.3672   -1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5904   -2.3038   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.6646    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -2.2706    1.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619   -2.9301    1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254   -2.8055   -0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   -0.3679    1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    0.7450    0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2642   -1.8180   -1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390   -0.1696   -2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189   -1.2104   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -1.3861    0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    1.2579   -1.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    1.0523    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262    0.0221   -1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410   -0.2171    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974    2.3092    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173    2.4692   -1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155    1.3969   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4157    2.8755    0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9504    1.3885    2.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0949   -0.0543    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6763   -0.6849    2.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 20 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z)-Octadecenoic acid	ChEBI
(Z)-Octadec-9-enoic acid	ChEBI
18:1 N-9	ChEBI
18:1DElta9cis	ChEBI
C18:1 N-9	ChEBI
cis-9-Octadecenoic acid	ChEBI
cis-Delta(9)-Octadecenoic acid	ChEBI
cis-Oleic acid	ChEBI
FA 18:1	ChEBI
Octadec-9-enoic acid	ChEBI
Oelsaeure	ChEBI
Oleate	ChEBI
(9Z)-Octadecenoate	Generator
(Z)-Octadec-9-enoate	Generator
cis-9-Octadecenoate	Generator
cis-delta(9)-Octadecenoate	Generator
cis-Δ(9)-octadecenoate	Generator
cis-Δ(9)-octadecenoic acid	Generator
cis-Oleate	Generator
Octadec-9-enoate	Generator
cis 9 Octadecenoic acid	MeSH
9 Octadecenoic acid	MeSH
9-Octadecenoic acid	MeSH
(9Z)-9-Octadecenoate	HMDB
(9Z)-9-Octadecenoic acid	HMDB
(Z)-9-Octadecanoate	HMDB
(Z)-9-Octadecanoic acid	HMDB
9,10-Octadecenoate	HMDB
9,10-Octadecenoic acid	HMDB
9-(Z)-Octadecenoate	HMDB
9-(Z)-Octadecenoic acid	HMDB
9-Octadecenoate	HMDB
Century CD fatty acid	HMDB
cis-Octadec-9-enoate	HMDB
cis-Octadec-9-enoic acid	HMDB
Distoline	HMDB
Emersol 210	HMDB
Emersol 211	HMDB
Emersol 213	HMDB
Emersol 220 white oleate	HMDB
Emersol 220 white oleic acid	HMDB
Emersol 221 low titer white oleate	HMDB
Emersol 221 low titer white oleic acid	HMDB
Emersol 233LL	HMDB
Emersol 6321	HMDB
Emersol 6333 NF	HMDB
Emersol 7021	HMDB
Glycon ro	HMDB
Glycon wo	HMDB
groco 2	HMDB
groco 4	HMDB
groco 5l	HMDB
groco 6	HMDB
Industrene 104	HMDB
Industrene 105	HMDB
Industrene 205	HMDB
Industrene 206	HMDB
L'acide oleique	HMDB
Metaupon	HMDB
Oelsauere	HMDB
Oleic acid extra pure	HMDB
Oleinate	HMDB
Oleinic acid	HMDB
Pamolyn	HMDB
Pamolyn 100	HMDB
Pamolyn 100 FG	HMDB
Pamolyn 100 FGK	HMDB
Pamolyn 125	HMDB
Priolene 6900	HMDB
Red oil	HMDB
tego-Oleic 130	HMDB
Vopcolene 27	HMDB
Wecoline oo	HMDB
Z-9-Octadecenoate	HMDB
Z-9-Octadecenoic acid	HMDB
Acid, 9-octadecenoic	MeSH, HMDB
Acid, oleic	MeSH, HMDB
Acid, cis-9-octadecenoic	MeSH, HMDB
FA(18:1(9Z))	HMDB
FA(18:1n9)	HMDB

Chemical Formula

C₁₈H₃₄O₂

Average Molecular Weight

282.4614

Monoisotopic Molecular Weight

282.255880332

IUPAC Name

(9Z)-octadec-9-enoic acid

Traditional Name

oleic acid

CAS Registry Number

112-80-1

SMILES

CCCCCCCC\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

InChI Key

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

octadec-9-enoic acid (CHEBI:16196 )
Unsaturated fatty acids (C00712 )
Monounsaturated fatty acids (C00712 )
Unsaturated fatty acids (LMFA01030002 )

Ontology

Adipose tissue (HMDB: HMDB0000207)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000207)

Epithelium

Epidermis (HMDB: HMDB0000207)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14634727)
Cerebrospinal Fluid (CSF) (PMID: 8412012)
Saliva (PMID: 20809147)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 2702744)
Feces (PMID: 19573517)

Cellular substructure

Membrane (HMDB: HMDB0000207)
Extracellular (HMDB: HMDB0000207)

Tissue substructure

Muscle (HMDB: HMDB0000207)

Stratum Corneum (HMDB: HMDB0000207)

Source

Exogenous

Exogenous (HMDB: HMDB0000207)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Oilseed crop

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Herbs and Spices (FooDB: FOOD00866)

Nut

Aquatic origin

Fish

Anchovy (FooDB: FOOD00566)
Blue whiting (FooDB: FOOD00567)
Carp bream (FooDB: FOOD00568)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Burbot (FooDB: FOOD00313)
Sturgeon (FooDB: FOOD00570)
Charr (FooDB: FOOD00571)
Gadus (Common cod) (FooDB: FOOD00515)
Common dab (FooDB: FOOD00574)
Spiny dogfish (FooDB: FOOD00575)
Anguilliformes (FooDB: FOOD00577)
Flatfish (FooDB: FOOD00535)
Garfish (FooDB: FOOD00579)
Haddock (FooDB: FOOD00374)
Gadiformes (FooDB: FOOD00580)
Atlantic halibut (FooDB: FOOD00516)
Greenland halibut/turbot (FooDB: FOOD00370)
Lake trout (FooDB: FOOD00582)
Lemon sole (FooDB: FOOD00583)
Common ling (FooDB: FOOD00397)
Lumpsucker (FooDB: FOOD00585)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Norway haddock (FooDB: FOOD00588)
Norway pout (FooDB: FOOD00590)
Perciformes (FooDB: FOOD00527)
Northern pike (FooDB: FOOD00431)
Pikeperch (FooDB: FOOD00595)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Pollock (FooDB: FOOD00513)
Rainbow trout (FooDB: FOOD00444)
Pacific ocean perch (FooDB: FOOD00598)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
Catfish (FooDB: FOOD00605)
Thunnus (FooDB: FOOD00607)
Turbot (FooDB: FOOD00364)
Whitefish (FooDB: FOOD00503)
Whiting (FooDB: FOOD00504)
Atlantic wolffish (FooDB: FOOD00296)

Crustacean

Fish product

Other fish product (FooDB: FOOD00665)

Amphibian

True frog (FooDB: FOOD00578)

Mollusk

Pinniped

True seal (FooDB: FOOD00600)

Seaweed

Kombu (FooDB: FOOD00602)
Agar (FooDB: FOOD00284)

Cetacean

Cetacea (Dolphin, Porpoise, Whale) (FooDB: FOOD00609)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Red raspberry (FooDB: FOOD00162)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)

Tropical fruit

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Fruit product

Other fruit product (FooDB: FOOD00765)
Fruit preserve (FooDB: FOOD00660)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Fruits (FooDB: FOOD00871)

Beverage

Distilled beverage

Spirit (FooDB: FOOD00276)
Liquor (FooDB: FOOD00616)
Whisky (FooDB: FOOD00623)

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Other beverage

Fortified wines

Sherry (FooDB: FOOD00632)
Vermouth (FooDB: FOOD00631)

Water

Water (FooDB: FOOD00664)

Alcoholic beverage

Other alcoholic beverage (FooDB: FOOD00278)
Alcoholic beverages (FooDB: FOOD00854)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Garden tomato (var.) (FooDB: FOOD00173)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Onion-family vegetable

Other vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Baby food

Baby food (FooDB: FOOD00668)

Animal origin

Swine

Domestic pig (FooDB: FOOD00536)

Bovine

Cattle (Beef, Veal) (FooDB: FOOD00495)

Poultry

Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Turkey (FooDB: FOOD00494)
Chicken (FooDB: FOOD00329)

Lagomorph

Mountain hare (FooDB: FOOD00581)
Rabbit (FooDB: FOOD00528)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Leavened bread

Wheat bread (FooDB: FOOD00808)
Rye bread (FooDB: FOOD00809)

Cereal

Barley (FooDB: FOOD00088)
Common buckwheat (FooDB: FOOD00079)
Corn (FooDB: FOOD00205)
Millet (FooDB: FOOD00126)
Oat (FooDB: FOOD00022)
Rice (FooDB: FOOD00125)
Rye (FooDB: FOOD00169)
Wheat (FooDB: FOOD00561)
Common wheat (FooDB: FOOD00187)
Hard wheat (FooDB: FOOD00242)
White bread (FooDB: FOOD00987)

Cereal product

Bread products

Other bread product (FooDB: FOOD00805)

Flat bread

Crisp bread (FooDB: FOOD00640)

Cereals and cereal products (FooDB: FOOD00858)

Baking good

Sugar

Sugar (FooDB: FOOD00651)

Dressing

Salad dressing (FooDB: FOOD00645)

Condiment

Substitute

Sugar substitute (FooDB: FOOD00656)

Seasoning

Salt (FooDB: FOOD00647)

Sauce

Sauce (FooDB: FOOD00646)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Miso (FooDB: FOOD00695)
Soy milk (FooDB: FOOD00736)
Soy sauce (FooDB: FOOD00694)
Tofu (FooDB: FOOD00696)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Dish

Ground meat

Sausage (FooDB: FOOD00652)
Meatball (FooDB: FOOD00653)
Pate (FooDB: FOOD00655)
Cold cut (FooDB: FOOD00770)

Other dish

Dumpling (FooDB: FOOD00669)
Other dish (FooDB: FOOD00836)
Pizza (FooDB: FOOD00637)
Soup (FooDB: FOOD00670)

Fat and oil

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)

Animal fat

Fish oil (FooDB: FOOD00990)
Fats and oils (FooDB: FOOD00864)

Milk and milk product

Other milk product

Butter (FooDB: FOOD00648)
Casein (FooDB: FOOD00659)
Whey (FooDB: FOOD00658)
Cream (FooDB: FOOD00650)
Dried milk (FooDB: FOOD00689)

Fermented milk product

Cheese (FooDB: FOOD00617)
Yogurt (FooDB: FOOD00620)
Ymer (FooDB: FOOD00638)

Unfermented milk

Fermented milk

Milk and milk products (FooDB: FOOD00863)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Confectionery

Candy

Dessert

Pastry (FooDB: FOOD00641)
Gelatin dessert (FooDB: FOOD00725)

Frozen dessert

Ice cream (FooDB: FOOD00624)
Other frozen dessert (FooDB: FOOD00729)

Other confectionery

Spread

Chocolate spread (FooDB: FOOD00676)

Cocoa and cocoa product

Cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Coffee and coffee product

Coffee

Snack

Cracker (FooDB: FOOD00787)
Other snack food (FooDB: FOOD00639)

Egg

Eggs (FooDB: FOOD00619)

Tea

Endogenous

Endogenous (HMDB: HMDB0000207)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Triacylglycerol Degradation TG(16:0/16:0/18:1(9Z)) (PathBank: SMP0012470)
Triacylglycerol Degradation TG(16:0/18:0/18:1(9Z)) (PathBank: SMP0012482)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/16:0) (PathBank: SMP0012492)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:0) (PathBank: SMP0012493)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0012494)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0012495)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0012496)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012497)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012498)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/20:0) (PathBank: SMP0012499)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/20:1(11Z)) (PathBank: SMP0012500)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/20:1(13Z)) (PathBank: SMP0012501)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/22:0) (PathBank: SMP0012502)
Triacylglycerol Degradation TG(16:0/18:1(9Z)/22:1(13Z)) (PathBank: SMP0012503)
Triacylglycerol Degradation TG(16:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0012506)
Triacylglycerol Degradation TG(16:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0012518)
Triacylglycerol Degradation TG(16:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012530)
Triacylglycerol Degradation TG(16:0/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0012542)
Triacylglycerol Degradation TG(16:0/20:0/18:1(9Z)) (PathBank: SMP0012554)
Triacylglycerol Degradation TG(16:0/20:1(11Z)/18:1(9Z)) (PathBank: SMP0012566)
Triacylglycerol Degradation TG(16:0/20:1(13Z)/18:1(9Z)) (PathBank: SMP0012578)
Triacylglycerol Degradation TG(16:0/22:0/18:1(9Z)) (PathBank: SMP0012590)
Triacylglycerol Degradation TG(16:0/22:1(13Z)/18:1(9Z)) (PathBank: SMP0012602)
Triacylglycerol Degradation TG(18:0/16:0/18:1(9Z)) (PathBank: SMP0012614)
Triacylglycerol Degradation TG(18:0/18:0/18:1(9Z)) (PathBank: SMP0012626)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/16:0) (PathBank: SMP0012636)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:0) (PathBank: SMP0012637)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0012638)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0012639)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0012640)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012641)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012642)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/20:0) (PathBank: SMP0012643)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/20:1(11Z)) (PathBank: SMP0012644)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/20:1(13Z)) (PathBank: SMP0012645)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/22:0) (PathBank: SMP0012646)
Triacylglycerol Degradation TG(18:0/18:1(9Z)/22:1(13Z)) (PathBank: SMP0012647)
Triacylglycerol Degradation TG(18:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0012650)
Triacylglycerol Degradation TG(18:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0012662)
Triacylglycerol Degradation TG(18:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012674)
Triacylglycerol Degradation TG(18:0/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0012686)
Triacylglycerol Degradation TG(18:0/20:0/18:1(9Z)) (PathBank: SMP0012698)
Triacylglycerol Degradation TG(18:0/20:1(11Z)/18:1(9Z)) (PathBank: SMP0012710)
Triacylglycerol Degradation TG(18:0/20:1(13Z)/18:1(9Z)) (PathBank: SMP0012722)
Triacylglycerol Degradation TG(18:0/22:0/18:1(9Z)) (PathBank: SMP0012734)
Triacylglycerol Degradation TG(18:0/22:1(13Z)/18:1(9Z)) (PathBank: SMP0012746)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/16:0) (PathBank: SMP0012756)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:0) (PathBank: SMP0012757)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:1(9Z)) (PathBank: SMP0012758)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:1(11Z)) (PathBank: SMP0012759)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:2(9Z,12Z)) (PathBank: SMP0012760)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012761)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0012762)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/20:0) (PathBank: SMP0012763)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/20:1(11Z)) (PathBank: SMP0012764)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/20:1(13Z)) (PathBank: SMP0012765)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/22:0) (PathBank: SMP0012766)
Triacylglycerol Degradation TG(18:1(9Z)/16:0/22:1(13Z)) (PathBank: SMP0012767)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/16:0) (PathBank: SMP0012768)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/18:0) (PathBank: SMP0012769)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/18:1(9Z)) (PathBank: SMP0012770)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/18:1(11Z)) (PathBank: SMP0012771)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/18:2(9Z,12Z)) (PathBank: SMP0012772)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012773)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0012774)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/20:0) (PathBank: SMP0012775)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/20:1(11Z)) (PathBank: SMP0012776)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/20:1(13Z)) (PathBank: SMP0012777)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/22:0) (PathBank: SMP0012778)
Triacylglycerol Degradation TG(18:1(9Z)/18:0/22:1(13Z)) (PathBank: SMP0012779)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/16:0) (PathBank: SMP0012780)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:0) (PathBank: SMP0012781)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0012782)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0012783)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0012784)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012785)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012786)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/20:0) (PathBank: SMP0012787)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0012788)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0012789)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/22:0) (PathBank: SMP0012790)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0012791)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/16:0) (PathBank: SMP0012792)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/18:0) (PathBank: SMP0012793)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0012794)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/18:1(11Z)) (PathBank: SMP0012795)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0012796)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012797)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012798)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/20:0) (PathBank: SMP0012799)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/20:1(11Z)) (PathBank: SMP0012800)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/20:1(13Z)) (PathBank: SMP0012801)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/22:0) (PathBank: SMP0012802)
Triacylglycerol Degradation TG(18:1(9Z)/18:1(11Z)/22:1(13Z)) (PathBank: SMP0012803)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/16:0) (PathBank: SMP0012804)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/18:0) (PathBank: SMP0012805)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0012806)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/18:1(11Z)) (PathBank: SMP0012807)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0012808)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012809)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012810)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/20:0) (PathBank: SMP0012811)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/20:1(11Z)) (PathBank: SMP0012812)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/20:1(13Z)) (PathBank: SMP0012813)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/22:0) (PathBank: SMP0012814)
Triacylglycerol Degradation TG(18:1(9Z)/18:2(9Z,12Z)/22:1(13Z)) (PathBank: SMP0012815)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/16:0) (PathBank: SMP0012816)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:0) (PathBank: SMP0012817)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012818)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(11Z)) (PathBank: SMP0012819)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0012820)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012821)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012822)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0012823)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0012824)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0012825)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0012826)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0012827)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/16:0) (PathBank: SMP0012828)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:0) (PathBank: SMP0012829)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0012830)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:1(11Z)) (PathBank: SMP0012831)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z)) (PathBank: SMP0012832)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012833)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012834)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0012835)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0012836)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0012837)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0012838)
Triacylglycerol Degradation TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0012839)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/16:0) (PathBank: SMP0012840)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/18:0) (PathBank: SMP0012841)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/18:1(9Z)) (PathBank: SMP0012842)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/18:1(11Z)) (PathBank: SMP0012843)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/18:2(9Z,12Z)) (PathBank: SMP0012844)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012845)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0012846)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/20:0) (PathBank: SMP0012847)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/20:1(11Z)) (PathBank: SMP0012848)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/20:1(13Z)) (PathBank: SMP0012849)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/22:0) (PathBank: SMP0012850)
Triacylglycerol Degradation TG(18:1(9Z)/20:0/22:1(13Z)) (PathBank: SMP0012851)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/16:0) (PathBank: SMP0012852)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/18:0) (PathBank: SMP0012853)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0012854)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/18:1(11Z)) (PathBank: SMP0012855)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0012856)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012857)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012858)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/20:0) (PathBank: SMP0012859)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/20:1(11Z)) (PathBank: SMP0012860)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/20:1(13Z)) (PathBank: SMP0012861)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/22:0) (PathBank: SMP0012862)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(11Z)/22:1(13Z)) (PathBank: SMP0012863)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/16:0) (PathBank: SMP0012864)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:0) (PathBank: SMP0012865)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0012866)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:1(11Z)) (PathBank: SMP0012867)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:2(9Z,12Z)) (PathBank: SMP0012868)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012869)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012870)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/20:0) (PathBank: SMP0012871)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/20:1(11Z)) (PathBank: SMP0012872)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/20:1(13Z)) (PathBank: SMP0012873)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/22:0) (PathBank: SMP0012874)
Triacylglycerol Degradation TG(18:1(9Z)/20:1(13Z)/22:1(13Z)) (PathBank: SMP0012875)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/16:0) (PathBank: SMP0012876)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/18:0) (PathBank: SMP0012877)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/18:1(9Z)) (PathBank: SMP0012878)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/18:1(11Z)) (PathBank: SMP0012879)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/18:2(9Z,12Z)) (PathBank: SMP0012880)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0012881)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0012882)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/20:0) (PathBank: SMP0012883)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/20:1(11Z)) (PathBank: SMP0012884)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/20:1(13Z)) (PathBank: SMP0012885)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/22:0) (PathBank: SMP0012886)
Triacylglycerol Degradation TG(18:1(9Z)/22:0/22:1(13Z)) (PathBank: SMP0012887)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/16:0) (PathBank: SMP0012888)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:0) (PathBank: SMP0012889)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0012890)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:1(11Z)) (PathBank: SMP0012891)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:2(9Z,12Z)) (PathBank: SMP0012892)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012893)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012894)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/20:0) (PathBank: SMP0012895)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/20:1(11Z)) (PathBank: SMP0012896)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/20:1(13Z)) (PathBank: SMP0012897)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/22:0) (PathBank: SMP0012898)
Triacylglycerol Degradation TG(18:1(9Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0012899)
Triacylglycerol Degradation TG(18:1(11Z)/16:0/18:1(9Z)) (PathBank: SMP0012902)
Triacylglycerol Degradation TG(18:1(11Z)/18:0/18:1(9Z)) (PathBank: SMP0012914)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/16:0) (PathBank: SMP0012924)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/18:0) (PathBank: SMP0012925)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0012926)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0012927)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0012928)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0012929)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0012930)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/20:0) (PathBank: SMP0012931)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0012932)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0012933)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/22:0) (PathBank: SMP0012934)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0012935)
Triacylglycerol Degradation TG(18:1(11Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0012938)
Triacylglycerol Degradation TG(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0012950)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0012962)
Triacylglycerol Degradation TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0012974)
Triacylglycerol Degradation TG(18:1(11Z)/20:0/18:1(9Z)) (PathBank: SMP0012986)
Triacylglycerol Degradation TG(18:1(11Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0012998)
Triacylglycerol Degradation TG(18:1(11Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013010)
Triacylglycerol Degradation TG(18:1(11Z)/22:0/18:1(9Z)) (PathBank: SMP0013022)
Triacylglycerol Degradation TG(18:1(11Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013034)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/16:0/18:1(9Z)) (PathBank: SMP0013046)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:0/18:1(9Z)) (PathBank: SMP0013058)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/16:0) (PathBank: SMP0013068)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/18:0) (PathBank: SMP0013069)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013070)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013071)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013072)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013073)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013074)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/20:0) (PathBank: SMP0013075)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013076)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013077)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/22:0) (PathBank: SMP0013078)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013079)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013082)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013094)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013106)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013118)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/20:0/18:1(9Z)) (PathBank: SMP0013130)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0013142)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013154)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/22:0/18:1(9Z)) (PathBank: SMP0013166)
Triacylglycerol Degradation TG(18:2(9Z,12Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013178)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/16:0/18:1(9Z)) (PathBank: SMP0013190)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:0/18:1(9Z)) (PathBank: SMP0013202)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/16:0) (PathBank: SMP0013212)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:0) (PathBank: SMP0013213)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013214)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013215)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013216)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013217)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013218)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/20:0) (PathBank: SMP0013219)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013220)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013221)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/22:0) (PathBank: SMP0013222)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013223)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013226)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013238)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013250)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013262)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:0/18:1(9Z)) (PathBank: SMP0013274)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0013286)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013298)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:0/18:1(9Z)) (PathBank: SMP0013310)
Triacylglycerol Degradation TG(18:3(6Z,9Z,12Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013322)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/16:0/18:1(9Z)) (PathBank: SMP0013334)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:0/18:1(9Z)) (PathBank: SMP0013346)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/16:0) (PathBank: SMP0013356)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:0) (PathBank: SMP0013357)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013358)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013359)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013360)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013361)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/20:0) (PathBank: SMP0013362)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013363)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013364)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/22:0) (PathBank: SMP0013365)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013366)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013369)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013380)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013391)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013403)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/20:0/18:1(9Z)) (PathBank: SMP0013415)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0013427)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013439)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/22:0/18:1(9Z)) (PathBank: SMP0013451)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013463)
Triacylglycerol Degradation TG(20:0/16:0/18:1(9Z)) (PathBank: SMP0013475)
Triacylglycerol Degradation TG(20:0/18:0/18:1(9Z)) (PathBank: SMP0013487)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/16:0) (PathBank: SMP0013497)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/18:0) (PathBank: SMP0013498)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013499)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013500)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013501)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013502)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013503)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/20:0) (PathBank: SMP0013504)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013505)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013506)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/22:0) (PathBank: SMP0013507)
Triacylglycerol Degradation TG(20:0/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013508)
Triacylglycerol Degradation TG(20:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013511)
Triacylglycerol Degradation TG(20:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013523)
Triacylglycerol Degradation TG(20:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013535)
Triacylglycerol Degradation TG(20:0/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013547)
Triacylglycerol Degradation TG(20:0/20:0/18:1(9Z)) (PathBank: SMP0013559)
Triacylglycerol Degradation TG(20:0/20:1(11Z)/18:1(9Z)) (PathBank: SMP0013571)
Triacylglycerol Degradation TG(20:0/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013583)
Triacylglycerol Degradation TG(20:0/22:0/18:1(9Z)) (PathBank: SMP0013595)
Triacylglycerol Degradation TG(20:0/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013607)
Triacylglycerol Degradation TG(20:1(11Z)/16:0/18:1(9Z)) (PathBank: SMP0013619)
Triacylglycerol Degradation TG(20:1(11Z)/18:0/18:1(9Z)) (PathBank: SMP0013631)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/16:0) (PathBank: SMP0013641)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/18:0) (PathBank: SMP0013642)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013643)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013644)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013645)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013646)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013647)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/20:0) (PathBank: SMP0013648)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013649)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013650)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/22:0) (PathBank: SMP0013651)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013652)
Triacylglycerol Degradation TG(20:1(11Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013655)
Triacylglycerol Degradation TG(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013667)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013679)
Triacylglycerol Degradation TG(20:1(11Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013691)
Triacylglycerol Degradation TG(20:1(11Z)/20:0/18:1(9Z)) (PathBank: SMP0013703)
Triacylglycerol Degradation TG(20:1(11Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0013715)
Triacylglycerol Degradation TG(20:1(11Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013727)
Triacylglycerol Degradation TG(20:1(11Z)/22:0/18:1(9Z)) (PathBank: SMP0013739)
Triacylglycerol Degradation TG(20:1(11Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013751)
Triacylglycerol Degradation TG(20:1(13Z)/16:0/18:1(9Z)) (PathBank: SMP0013764)
Triacylglycerol Degradation TG(20:1(13Z)/18:0/18:1(9Z)) (PathBank: SMP0013776)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/16:0) (PathBank: SMP0013786)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/18:0) (PathBank: SMP0013787)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013788)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013789)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013790)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013791)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013792)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/20:0) (PathBank: SMP0013793)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013794)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013795)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/22:0) (PathBank: SMP0013796)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013797)
Triacylglycerol Degradation TG(20:1(13Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013800)
Triacylglycerol Degradation TG(20:1(13Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013812)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013824)
Triacylglycerol Degradation TG(20:1(13Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013836)
Triacylglycerol Degradation TG(20:1(13Z)/20:0/18:1(9Z)) (PathBank: SMP0013848)
Triacylglycerol Degradation TG(20:1(13Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0013860)
Triacylglycerol Degradation TG(20:1(13Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0013872)
Triacylglycerol Degradation TG(20:1(13Z)/22:0/18:1(9Z)) (PathBank: SMP0013884)
Triacylglycerol Degradation TG(20:1(13Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0013897)
Triacylglycerol Degradation TG(22:0/16:0/18:1(9Z)) (PathBank: SMP0013909)
Triacylglycerol Degradation TG(22:0/18:0/18:1(9Z)) (PathBank: SMP0013921)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/16:0) (PathBank: SMP0013931)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/18:0) (PathBank: SMP0013932)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0013933)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0013934)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0013935)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0013936)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0013937)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/20:0) (PathBank: SMP0013938)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/20:1(11Z)) (PathBank: SMP0013939)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/20:1(13Z)) (PathBank: SMP0013940)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/22:0) (PathBank: SMP0013941)
Triacylglycerol Degradation TG(22:0/18:1(9Z)/22:1(13Z)) (PathBank: SMP0013942)
Triacylglycerol Degradation TG(22:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0013945)
Triacylglycerol Degradation TG(22:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0013957)
Triacylglycerol Degradation TG(22:0/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0013969)
Triacylglycerol Degradation TG(22:0/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0013981)
Triacylglycerol Degradation TG(22:0/20:0/18:1(9Z)) (PathBank: SMP0013993)
Triacylglycerol Degradation TG(22:0/20:1(11Z)/18:1(9Z)) (PathBank: SMP0014005)
Triacylglycerol Degradation TG(22:0/20:1(13Z)/18:1(9Z)) (PathBank: SMP0014019)
Triacylglycerol Degradation TG(22:0/22:0/18:1(9Z)) (PathBank: SMP0014031)
Triacylglycerol Degradation TG(22:0/22:1(13Z)/18:1(9Z)) (PathBank: SMP0014043)
Triacylglycerol Degradation TG(22:1(13Z)/16:0/18:1(9Z)) (PathBank: SMP0014055)
Triacylglycerol Degradation TG(22:1(13Z)/18:0/18:1(9Z)) (PathBank: SMP0014067)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/16:0) (PathBank: SMP0014077)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/18:0) (PathBank: SMP0014078)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0014079)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0014080)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0014081)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0014082)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0014083)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/20:0) (PathBank: SMP0014084)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/20:1(11Z)) (PathBank: SMP0014086)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/22:0) (PathBank: SMP0014087)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/22:1(13Z)) (PathBank: SMP0014088)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0014091)
Triacylglycerol Degradation TG(22:1(13Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0014103)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) (PathBank: SMP0014115)
Triacylglycerol Degradation TG(22:1(13Z)/18:3(9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0014127)
Triacylglycerol Degradation TG(22:1(13Z)/20:0/18:1(9Z)) (PathBank: SMP0014139)
Triacylglycerol Degradation TG(22:1(13Z)/20:1(11Z)/18:1(9Z)) (PathBank: SMP0014151)
Triacylglycerol Degradation TG(22:1(13Z)/20:1(13Z)/18:1(9Z)) (PathBank: SMP0014164)
Triacylglycerol Degradation TG(22:1(13Z)/22:0/18:1(9Z)) (PathBank: SMP0014176)
Triacylglycerol Degradation TG(22:1(13Z)/22:1(13Z)/18:1(9Z)) (PathBank: SMP0014188)
Triacylglycerol Degradation TG(22:1(13Z)/18:1(9Z)/20:1(13Z)) (PathBank: SMP0014198)
Triacylglycerol Degradation TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0014199)

5alpha-reductase inhibitor (HMDB: HMDB0000207)
Androgen antagonist (HMDB: HMDB0000207)
Androgen antagonist (HMDB: HMDB0000207)
Alpha-reductase inhibitor (HMDB: HMDB0000207)

EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor (HMDB: HMDB0000207)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0000207)

Biomarker

Diabetes mellitus type 2 (MarkerDB: MDB00029979)
Isovaleric acidemia (MarkerDB: MDB00029979)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0000207)

Fragrance (HMDB: HMDB0000207)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	13.4 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	173.875	30932474
[M-H]-	Not Available	175.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000183

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00012 g/L	ALOGPS
logP	7.68	ALOGPS
logP	6.78	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	87.4 m³·mol⁻¹	ChemAxon
Polarizability	37.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.565	31661259
DarkChem	[M-H]-	177.265	31661259
AllCCS	[M+H]+	179.569	32859911
AllCCS	[M-H]-	179.428	32859911
DeepCCS	[M+H]+	180.771	30932474
DeepCCS	[M-H]-	176.752	30932474
DeepCCS	[M-2H]-	213.903	30932474
DeepCCS	[M+Na]+	189.828	30932474
AllCCS	[M+H]+	179.6	32859911
AllCCS	[M+H-H2O]+	176.6	32859911
AllCCS	[M+NH4]+	182.3	32859911
AllCCS	[M+Na]+	183.1	32859911
AllCCS	[M-H]-	179.4	32859911
AllCCS	[M+Na-2H]-	181.0	32859911
AllCCS	[M+HCOO]-	182.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oleic acid	CCCCCCCC\C=C/CCCCCCCC(O)=O	3141.2	Standard polar	33892256
Oleic acid	CCCCCCCC\C=C/CCCCCCCC(O)=O	2093.8	Standard non polar	33892256
Oleic acid	CCCCCCCC\C=C/CCCCCCCC(O)=O	2150.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oleic acid,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2217.5	Semi standard non polar	33892256
Oleic acid,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2477.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Oleic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00vi-9500000000-cdb5366d3ece43c3e166	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleic acid GC-MS (1 TMS)	splash10-00nb-5900000000-fc03835c9c8fddb27970	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleic acid EI-B (Non-derivatized)	splash10-052f-9100000000-7618883a87bd14687fd5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleic acid GC-EI-TOF (Non-derivatized)	splash10-00vi-9500000000-cdb5366d3ece43c3e166	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleic acid GC-MS (Non-derivatized)	splash10-00nb-5900000000-fc03835c9c8fddb27970	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9640000000-29b5681d79890854ef2b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0fe0-9431000000-1879934642ac672cb401	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9100000000-350dc6d7ac541a3c5b67	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00ls-4790000000-d753b2905852ca2a8cbd	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0aou-9000000000-64594906d693e8a08650	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-00l2-4790000000-aefa66e9f83fcb24ead6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0apm-9100000000-a71c58b95cb65487eeed	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0aou-9000000000-5889cbe3dd606123df50	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative-QTOF	splash10-001i-0090000000-89531b488fbe899c09e6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid EI-B (Unknown) , Positive-QTOF	splash10-052f-9100000000-de078efada08e691dbb8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF 20V, Negative-QTOF	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF 30V, Negative-QTOF	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF , Negative-QTOF	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF 10V, Negative-QTOF	splash10-001i-0090000000-92096c6b229762c5295f	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF 20V, Negative-QTOF	splash10-001i-0090000000-5fe8495a19b387bf702c	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF 30V, Negative-QTOF	splash10-001i-0090000000-5d40399b1c736b476445	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF , Negative-QTOF	splash10-001i-0090000000-45785aeb659bd8a09240	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid ESI-TOF 10V, Negative-QTOF	splash10-001i-0091000000-3946ac7663105c7c2700	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid LC-ESI-IT , negative-QTOF	splash10-001i-0090000000-ce1372cb3b5e84122349	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleic acid LC-ESI-TOF , negative-QTOF	splash10-001i-0090000000-92096c6b229762c5295f	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleic acid 10V, Positive-QTOF	splash10-00lr-0090000000-755e8d1537818580a2fd	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleic acid 20V, Positive-QTOF	splash10-00y0-4690000000-ca39c5846217fe093227	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleic acid 40V, Positive-QTOF	splash10-0596-9830000000-fcb2923d448d11c54559	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleic acid 10V, Negative-QTOF	splash10-001i-0090000000-e809fd7222cf63431b77	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleic acid 20V, Negative-QTOF	splash10-001r-1090000000-9c340e3d19cbe7013ccd	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleic acid 40V, Negative-QTOF	splash10-0a4l-9230000000-6e517cda629fcd4df07d	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Adipose Tissue
Epidermis
Intestine
Liver
Pancreas
Placenta
Prostate
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	11.42 +/- 1.67 uM	Adult (>18 years old)	Both	Normal	14634727	details
Blood	Detected and Quantified	122 +/- 56 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24789758	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	346.950 +/- 38.943 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	332.789 +/- 49.564 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	339.869 +/- 42.484 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	339.869 +/- 31.863 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	130 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	131 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	158 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	191 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	202 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	236 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	240 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	246 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	248 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	257 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	267 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	284 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	476.384 +/- 146.817 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	401.329 +/- 90.915 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	49.243 +/- 19.314 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	37.0 +/- 5.7 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	32.5-41.3 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	2135.4 +/- 665.5 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Blood	Detected and Quantified	80.3 +/- 9.331 uM	Adult (>18 years old)	Both	Normal	20671299	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	36.0 +/- 36.0 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected and Quantified	55.0518 +/- 80.0463 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28587349	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	1268322	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	5.2 (0.3-13) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	0.16 +/- 0.08 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	10.22 +/- 1.33 uM	Adult (>18 years old)	Female	Gestational diabetes mellitus (GDM)	14634727	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Lung cancer	25961003	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	24789758	details
Blood	Detected and Quantified	2365.1 +/- 844.5 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22007635	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	28587349	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details

Associated Disorders and Diseases

Disease References

Gestational diabetes
Min Y, Ghebremeskel K, Lowy C, Thomas B, Crawford MA: Adverse effect of obesity on red cell membrane arachidonic and docosahexaenoic acids in gestational diabetes. Diabetologia. 2004 Jan;47(1):75-81. Epub 2003 Nov 22. [PubMed:14634727 ]
Lung Cancer
Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
Schizophrenia
Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ] Al Awam K, Haussleiter IS, Dudley E, Donev R, Brune M, Juckel G, Thome J: Multiplatform metabolome and proteome profiling identifies serum metabolite and protein signatures as prospective biomarkers for schizophrenia. J Neural Transm (Vienna). 2015 Aug;122 Suppl 1:S111-22. doi: 10.1007/s00702-014-1224-0. Epub 2014 May 1. [PubMed:24789758 ]
Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ] Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]

Associated OMIM IDs

211980 (Lung Cancer)
181500 (Schizophrenia)
243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Oleic_acid

METLIN ID

190

PubChem Compound

445639

PDB ID

Not Available

ChEBI ID

16196

Food Biomarker Ontology

Not Available

VMH ID

OCDCEA

MarkerDB ID

MDB00029979

Good Scents ID

rw1029521

References

Synthesis Reference

Hu, Sheng; Yuan, Ji-rong; Zhu, Jin; Yin, Ying-sui. Preparation of high-purity oleic acid by selective reaction. Yingyong Huagong (2005), 34(12), 748-750, 753.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
Takahashi K, Rytting JH: Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane. J Pharm Pharmacol. 2001 Jun;53(6):789-94. [PubMed:11428654 ]
Jensen MD: Gender differences in regional fatty acid metabolism before and after meal ingestion. J Clin Invest. 1995 Nov;96(5):2297-303. [PubMed:7593616 ]
Russell AP, Somm E, Debigare R, Hartley O, Richard D, Gastaldi G, Melotti A, Michaud A, Giacobino JP, Muzzin P, LeBlanc P, Maltais F: COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers. J Cardiopulm Rehabil. 2004 Sep-Oct;24(5):332-9. [PubMed:15602154 ]
Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. [PubMed:10391868 ]
Colette C, Percheron C, Pares-Herbute N, Michel F, Pham TC, Brillant L, Descomps B, Monnier L: Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors. Int J Obes Relat Metab Disord. 2003 Jun;27(6):648-56. [PubMed:12833107 ]
Christophe AB, De Greyt WF, Delanghe JR, Huyghebaert AD: Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man. Ann Nutr Metab. 2000;44(2):61-7. [PubMed:10970994 ]
de la Maza MP, Hirsch S, Nieto S, Petermann M, Bunout D: Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage. Alcohol Clin Exp Res. 1996 Nov;20(8):1418-22. [PubMed:8947319 ]
Droke EA, Briske-Anderson M, Lukaski HC: Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells. Biol Trace Elem Res. 2003 Dec;95(3):219-32. [PubMed:14665727 ]
Valjakka-Koskela R, Hirvonen J, Monkkonen J, Kiesvaara J, Antila S, Lehtonen L, Urtti A: Transdermal delivery of levosimendan. Eur J Pharm Sci. 2000 Oct;11(4):343-50. [PubMed:11033078 ]
Jones AE, Stolinski M, Smith RD, Murphy JL, Wootton SA: Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women. Br J Nutr. 1999 Jan;81(1):37-43. [PubMed:10341674 ]
Thielitz A, Helmdach M, Ropke EM, Gollnick H: Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. Br J Dermatol. 2001 Jul;145(1):19-27. [PubMed:11453902 ]
Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30. [PubMed:7929039 ]
Lima WP, Carnevali LC Jr, Eder R, Costa Rosa LF, Bacchi EM, Seelaender MC: Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation. Clin Nutr. 2005 Dec;24(6):1019-28. Epub 2005 Sep 22. [PubMed:16182414 ]
Vinggaard AM, Provost JJ, Exton JH, Hansen HS: Arf and RhoA regulate both the cytosolic and the membrane-bound phospholipase D from human placenta. Cell Signal. 1997 Feb;9(2):189-96. [PubMed:9113419 ]
Mittendorfer B, Liem O, Patterson BW, Miles JM, Klein S: What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean? Diabetes. 2003 Jul;52(7):1641-8. [PubMed:12829627 ]
Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. [PubMed:11124748 ]
Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53. [PubMed:16249438 ]
Andersen TC, Pedersen JF, Nordentoft T, Olsen O: Fat and mesenteric blood flow. Scand J Gastroenterol. 1999 Sep;34(9):894-7. [PubMed:10522608 ]
Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Kalia YN, Cornejo-Bravo JM, Ganem-Quintanar A: Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res. 2003 Aug;20(8):1267-73. [PubMed:12948025 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Reactions

Oleoyl-[acyl-carrier-protein] + Water → [acyl-carrier-protein] + Oleic acid	details

Enzyme Details

2. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

3. Cytosolic acyl coenzyme A thioester hydrolase

General function:: Lipid transport and metabolism
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:: ACOT7
Uniprot ID:: O00154
Molecular weight:: 40454.945

Reactions

Oleoyl-CoA + Water → Coenzyme A + Oleic acid	details

Enzyme Details

4. Acyl-coenzyme A thioesterase 2, mitochondrial

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:: ACOT2
Uniprot ID:: P49753
Molecular weight:: 53218.02

Reactions

Oleoyl-CoA + Water → Coenzyme A + Oleic acid	details

Enzyme Details

5. Acyl-coenzyme A thioesterase 4

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:: ACOT4
Uniprot ID:: Q8N9L9
Molecular weight:: 46326.09

Reactions

Oleoyl-CoA + Water → Coenzyme A + Oleic acid	details

Enzyme Details

6. Acyl-coenzyme A thioesterase 8

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:: ACOT8
Uniprot ID:: O14734
Molecular weight:: 35914.02

Enzyme Details

7. Fatty-acid amide hydrolase 1

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:: FAAH
Uniprot ID:: O00519
Molecular weight:: 63065.28

Reactions

Oleamide + Water → Oleic acid + Ammonia	details

Enzyme Details

8. 2-acylglycerol O-acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Has a preference toward monoacylglycerols containing unsaturated fatty acids in an order of C18:3 > C18:2 > C18:1 > C18:0. Plays a central role in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes. May play a role in diet-induced obesity.
Gene Name:: MOGAT2
Uniprot ID:: Q3SYC2
Molecular weight:: 38195.285

Enzyme Details

9. Fatty-acid amide hydrolase 2

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:: FAAH2
Uniprot ID:: Q6GMR7
Molecular weight:: 58303.115

Reactions

Oleamide + Water → Oleic acid + Ammonia	details

Enzyme Details

10. Acyl-coenzyme A thioesterase 1

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:: ACOT1
Uniprot ID:: Q86TX2
Molecular weight:: 46276.96

Reactions

Oleoyl-CoA + Water → Coenzyme A + Oleic acid	details

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Oleic acid (HMDB0000207)

MOL for HMDB0000207 (Oleic acid)

3D MOL for HMDB0000207 (Oleic acid)

3D SDF for HMDB0000207 (Oleic acid)

3D-SDF for HMDB0000207 (Oleic acid)

PDB for HMDB0000207 (Oleic acid)

3D PDB for HMDB0000207 (Oleic acid)

SMILES for HMDB0000207 (Oleic acid)

INCHI for HMDB0000207 (Oleic acid)

Structure for HMDB0000207 (Oleic acid)

3D Structure for HMDB0000207 (Oleic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions