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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (13)transporters (1) Show 14 proteins XML

enzymes (13)transporters (1) Show 14 proteins

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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000244

Secondary Accession Numbers

HMDB00244

Metabolite Identification

Common Name

Riboflavin

Description

Riboflavin or vitamin B2 is an easily absorbed, water-soluble micronutrient with a key role in maintaining human health. Like the other B vitamins, it supports energy production by aiding in the metabolizing of fats, carbohydrates, and proteins. Vitamin B2 is also required for red blood cell formation and respiration, antibody production, and for regulating human growth and reproduction. It is essential for healthy skin, nails, hair growth and general good health, including regulating thyroid activity. Riboflavin is found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. Riboflavin is yellow or orange-yellow in color and in addition to being used as a food coloring it is also used to fortify some foods. It can be found in baby foods, breakfast cereals, sauces, processed cheese, fruit drinks and vitamin-enriched milk products. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin adenine dinucleotide.

Structure

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

  Mrv1652308122017442D          

 27 29  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16  3  1  0  0  0  0
 16  1  1  0  0  0  0
  4 10  1  0  0  0  0
 10  2  2  0  0  0  0
 11  1  2  0  0  0  0
  2  1  1  0  0  0  0
  2 12  1  0  0  0  0
 11  9  1  0  0  0  0
 12 15  1  0  0  0  0
 15  9  1  0  0  0  0
  5  3  2  0  0  0  0
  3  4  1  0  0  0  0
  6  4  2  0  0  0  0
  5  8  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  9 14  2  0  0  0  0
 12 13  2  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
 18 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  1  0  0  0
 21 23  1  0  0  0  0
 21 24  1  6  0  0  0
 23 25  1  0  0  0  0
  8 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

HMDB0000244
     RDKit          3D
Riboflavin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.5779   -2.3163    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.4736    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -0.1066    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.7205    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977    2.0538    0.5420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    2.9100    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    4.2765    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875    4.7839    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    5.0504   -0.1972 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    4.5229   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    5.3224   -1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    3.1986   -0.7247 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    2.3189   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855    0.9800   -0.4146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    0.5316   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.4044    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5609   -0.4759    1.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.2491   -0.3813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3146    0.3358    0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.9685   -1.2228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6592   -0.8027   -1.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -2.2320   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -2.6276    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    0.1958   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.1649   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747   -1.9822    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857   -3.4574    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973   -3.3040    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -1.8007    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5536   -2.3702    2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3092    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    6.0903   -0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3394   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8265   -0.3501   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173    1.4581    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -0.1967    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4675    1.1620   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    1.2301    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -1.0677   -1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -1.4424   -2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -3.0549   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -2.1329    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -3.0852    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -1.5688   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730   -3.9864    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -3.6599    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -3.8158   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  2  1  0
 24  4  2  0
 13  6  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  9 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  6
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
M  END

  Mrv1652308122017442D          

 27 29  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16  3  1  0  0  0  0
 16  1  1  0  0  0  0
  4 10  1  0  0  0  0
 10  2  2  0  0  0  0
 11  1  2  0  0  0  0
  2  1  1  0  0  0  0
  2 12  1  0  0  0  0
 11  9  1  0  0  0  0
 12 15  1  0  0  0  0
 15  9  1  0  0  0  0
  5  3  2  0  0  0  0
  3  4  1  0  0  0  0
  6  4  2  0  0  0  0
  5  8  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  9 14  2  0  0  0  0
 12 13  2  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
 18 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  1  0  0  0
 21 23  1  0  0  0  0
 21 24  1  6  0  0  0
 23 25  1  0  0  0  0
  8 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000244

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1

> <INCHI_KEY>
AUNGANRZJHBGPY-SCRDCRAPSA-N

> <FORMULA>
C17H20N4O6

> <MOLECULAR_WEIGHT>
376.3639

> <EXACT_MASS>
376.138284392

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.50970932405913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-0.9165402600000004

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.852833299641368

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.969939364997856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.610702399953126

> <JCHEM_POLAR_SURFACE_AREA>
155.04999999999998

> <JCHEM_REFRACTIVITY>
96.2684

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
riboflavin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000244
     RDKit          3D
Riboflavin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.5779   -2.3163    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.4736    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -0.1066    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.7205    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977    2.0538    0.5420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    2.9100    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    4.2765    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875    4.7839    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    5.0504   -0.1972 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    4.5229   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    5.3224   -1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    3.1986   -0.7247 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    2.3189   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855    0.9800   -0.4146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    0.5316   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.4044    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5609   -0.4759    1.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.2491   -0.3813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3146    0.3358    0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.9685   -1.2228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6592   -0.8027   -1.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -2.2320   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -2.6276    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    0.1958   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.1649   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747   -1.9822    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857   -3.4574    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973   -3.3040    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -1.8007    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5536   -2.3702    2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3092    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    6.0903   -0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3394   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8265   -0.3501   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173    1.4581    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -0.1967    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4675    1.1620   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    1.2301    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -1.0677   -1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -1.4424   -2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -3.0549   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -2.1329    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -3.0852    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -1.5688   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730   -3.9864    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -3.6599    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -3.8158   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  2  1  0
 24  4  2  0
 13  6  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  9 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  6
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
M  END

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001   5.390   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
CONECT    1   16   11    2                                                  
CONECT    2   10    1   12                                                  
CONECT    3   16    5    4                                                  
CONECT    4   10    3    6                                                  
CONECT    5    3    8                                                       
CONECT    6    4    7                                                       
CONECT    7    8    6   27                                                  
CONECT    8    5    7   26                                                  
CONECT    9   11   15   14                                                  
CONECT   10    4    2                                                       
CONECT   11    1    9                                                       
CONECT   12    2   15   13                                                  
CONECT   13   12                                                            
CONECT   14    9                                                            
CONECT   15   12    9                                                       
CONECT   16    3    1   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21   22                                                  
CONECT   20   18                                                            
CONECT   21   19   23   24                                                  
CONECT   22   19                                                            
CONECT   23   21   25                                                       
CONECT   24   21                                                            
CONECT   25   23                                                            
CONECT   26    8                                                            
CONECT   27    7                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0000244
HETATM    1  C1  UNL     1       4.578  -2.316   1.269  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.444  -1.474   0.815  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.610  -0.107   0.877  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.581   0.720   0.464  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.798   2.054   0.542  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.837   2.910   0.153  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.019   4.277   0.216  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.088   4.784   0.639  1.00  0.00           O  
HETATM    9  N2  UNL     1       0.999   5.050  -0.197  1.00  0.00           N  
HETATM   10  C7  UNL     1      -0.146   4.523  -0.651  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.060   5.322  -1.021  1.00  0.00           O  
HETATM   12  N3  UNL     1      -0.353   3.199  -0.725  1.00  0.00           N  
HETATM   13  C8  UNL     1       0.599   2.319  -0.338  1.00  0.00           C  
HETATM   14  N4  UNL     1       0.386   0.980  -0.415  1.00  0.00           N  
HETATM   15  C9  UNL     1      -0.879   0.532  -0.918  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.912   0.404   0.208  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.561  -0.476   1.185  1.00  0.00           O  
HETATM   18  C11 UNL     1      -3.276   0.249  -0.381  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.315   0.336   0.535  1.00  0.00           O  
HETATM   20  C12 UNL     1      -3.419  -0.969  -1.223  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.659  -0.803  -1.928  1.00  0.00           O  
HETATM   22  C13 UNL     1      -3.542  -2.232  -0.439  1.00  0.00           C  
HETATM   23  O6  UNL     1      -2.460  -2.628   0.285  1.00  0.00           O  
HETATM   24  C14 UNL     1       1.379   0.196  -0.013  1.00  0.00           C  
HETATM   25  C15 UNL     1       1.239  -1.165  -0.065  1.00  0.00           C  
HETATM   26  C16 UNL     1       2.275  -1.982   0.350  1.00  0.00           C  
HETATM   27  C17 UNL     1       2.086  -3.457   0.280  1.00  0.00           C  
HETATM   28  H1  UNL     1       4.597  -3.304   0.766  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.514  -1.801   0.974  1.00  0.00           H  
HETATM   30  H3  UNL     1       4.554  -2.370   2.364  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.542   0.309   1.246  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.125   6.090  -0.154  1.00  0.00           H  
HETATM   33  H6  UNL     1      -1.282   1.339  -1.576  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.826  -0.350  -1.561  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.917   1.458   0.662  1.00  0.00           H  
HETATM   36  H9  UNL     1      -1.893  -0.197   2.067  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.468   1.162  -1.077  1.00  0.00           H  
HETATM   38  H11 UNL     1      -4.394   1.230   0.935  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.655  -1.068  -1.995  1.00  0.00           H  
HETATM   40  H13 UNL     1      -4.639  -1.442  -2.681  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.743  -3.055  -1.189  1.00  0.00           H  
HETATM   42  H15 UNL     1      -4.437  -2.133   0.220  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.706  -3.085   1.111  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.319  -1.569  -0.435  1.00  0.00           H  
HETATM   45  H18 UNL     1       2.673  -3.986   1.054  1.00  0.00           H  
HETATM   46  H19 UNL     1       1.011  -3.660   0.504  1.00  0.00           H  
HETATM   47  H20 UNL     1       2.294  -3.816  -0.738  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3   26
CONECT    3    4   31
CONECT    4    5   24   24
CONECT    5    6    6
CONECT    6    7   13
CONECT    7    8    8    9
CONECT    9   10   32
CONECT   10   11   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   24
CONECT   15   16   33   34
CONECT   16   17   18   35
CONECT   17   36
CONECT   18   19   20   37
CONECT   19   38
CONECT   20   21   22   39
CONECT   21   40
CONECT   22   23   41   42
CONECT   23   43
CONECT   24   25
CONECT   25   26   26   44
CONECT   26   27
CONECT   27   45   46   47
END

HMDB0000244
     RDKit          3D
Riboflavin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.5779   -2.3163    1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.4736    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -0.1066    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.7205    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977    2.0538    0.5420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374    2.9100    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    4.2765    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875    4.7839    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    5.0504   -0.1972 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465    4.5229   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598    5.3224   -1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    3.1986   -0.7247 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992    2.3189   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3855    0.9800   -0.4146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    0.5316   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.4044    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5609   -0.4759    1.1845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.2491   -0.3813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3146    0.3358    0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187   -0.9685   -1.2228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6592   -0.8027   -1.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5423   -2.2320   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -2.6276    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793    0.1958   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.1649   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747   -1.9822    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857   -3.4574    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5973   -3.3040    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -1.8007    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5536   -2.3702    2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3092    1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1247    6.0903   -0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    1.3394   -1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8265   -0.3501   -1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173    1.4581    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -0.1967    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4675    1.1620   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    1.2301    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -1.0677   -1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393   -1.4424   -2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433   -3.0549   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -2.1329    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -3.0852    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -1.5688   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730   -3.9864    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115   -3.6599    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -3.8158   -0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  2  1  0
 24  4  2  0
 13  6  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  9 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  6
 19 38  1  0
 20 39  1  6
 21 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
 27 45  1  0
 27 46  1  0
 27 47  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol	ChEBI
6,7-Dimethyl-9-D-ribitylisoalloxazine	ChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione	ChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine	ChEBI
7,8-Dimethyl-10-ribitylisoalloxazine	ChEBI
e101	ChEBI
Lactoflavin	ChEBI
Riboflavina	ChEBI
RIBOFLAVINE	ChEBI
Riboflavinum	ChEBI
Vitamin b2	ChEBI
Vitamin g	ChEBI
Bisulase	Kegg
(-)-Riboflavin	HMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol	HMDB
6,7-Dimethyl-9-ribitylisoalloxazine	HMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dione	HMDB
Beflavin	HMDB
Beflavine	HMDB
Benzo[g]pteridine riboflavin deriv.	HMDB
e 101	HMDB
Flavaxin	HMDB
Flavin BB	HMDB
Flaxain	HMDB
FOOD Yellow 15	HMDB
Hyre	HMDB
Lactobene	HMDB
Lactoflavine	HMDB
Ribipca	HMDB
Ribocrisina	HMDB
Riboderm	HMDB
Ribosyn	HMDB
Ribotone	HMDB
Ribovel	HMDB
Russupteridine yellow III	HMDB
San yellow b	HMDB
Vitaflavine	HMDB
Vitasan b2	HMDB
Vitamin b 2	HMDB

Chemical Formula

C₁₇H₂₀N₄O₆

Average Molecular Weight

376.3639

Monoisotopic Molecular Weight

376.138284392

IUPAC Name

7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

Traditional Name

riboflavin

CAS Registry Number

83-88-5

SMILES

CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1

InChI Identifier

InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1

InChI Key

AUNGANRZJHBGPY-SCRDCRAPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Alloxazines and isoalloxazines

Direct Parent

Flavins

Alternative Parents

Substituents

Flavin
Diazanaphthalene
Quinoxaline
Pyrimidone
Pyrazine
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Polyol
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin (CHEBI:17015 )
Water-soluble vitamins (C00255 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.085 mg/mL	Not Available
LogP	-1.46	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	189.346	30932474
[M+H]+	Baker	192.429	30932474
[M-H]-	Not Available	186.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000318
[M+H]+	Not Available	189.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000318

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.92	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.97	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.27 m³·mol⁻¹	ChemAxon
Polarizability	37.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	185.363	31661259
DarkChem	[M-H]-	182.131	31661259
AllCCS	[M+H]+	185.99	32859911
AllCCS	[M-H]-	184.627	32859911
DeepCCS	[M+H]+	190.808	30932474
DeepCCS	[M-H]-	188.412	30932474
DeepCCS	[M-2H]-	221.341	30932474
DeepCCS	[M+Na]+	196.72	30932474
AllCCS	[M+H]+	186.0	32859911
AllCCS	[M+H-H2O]+	183.4	32859911
AllCCS	[M+NH4]+	188.3	32859911
AllCCS	[M+Na]+	189.0	32859911
AllCCS	[M-H]-	184.6	32859911
AllCCS	[M+Na-2H]-	184.6	32859911
AllCCS	[M+HCOO]-	184.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Riboflavin	CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1	4211.2	Standard polar	33892256
Riboflavin	CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1	2384.1	Standard non polar	33892256
Riboflavin	CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1	3964.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Riboflavin,1TMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CO)C1=NC(=O)[NH]C(=O)C1=N2	3392.8	Semi standard non polar	33892256
Riboflavin,1TMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CO)C1=NC(=O)[NH]C(=O)C1=N2	3382.0	Semi standard non polar	33892256
Riboflavin,1TMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3409.4	Semi standard non polar	33892256
Riboflavin,1TMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3394.7	Semi standard non polar	33892256
Riboflavin,1TMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3515.4	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CO)C1=NC(=O)[NH]C(=O)C1=N2	3254.6	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #10	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3387.2	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3291.1	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3265.2	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3377.3	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3260.1	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #6	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3249.5	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #7	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3371.4	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #8	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3280.7	Semi standard non polar	33892256
Riboflavin,2TMS,isomer #9	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3394.6	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3224.1	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #10	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3313.4	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3202.8	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3304.1	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3224.0	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3320.7	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #6	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3310.0	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #7	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3216.8	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #8	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3299.5	Semi standard non polar	33892256
Riboflavin,3TMS,isomer #9	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3288.2	Semi standard non polar	33892256
Riboflavin,4TMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3235.5	Semi standard non polar	33892256
Riboflavin,4TMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3306.4	Semi standard non polar	33892256
Riboflavin,4TMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3269.7	Semi standard non polar	33892256
Riboflavin,4TMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3295.9	Semi standard non polar	33892256
Riboflavin,4TMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3292.5	Semi standard non polar	33892256
Riboflavin,5TMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3325.1	Semi standard non polar	33892256
Riboflavin,5TMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3384.4	Standard non polar	33892256
Riboflavin,5TMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C(=O)C1=N2	3909.1	Standard polar	33892256
Riboflavin,1TBDMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)CO)C1=NC(=O)[NH]C(=O)C1=N2	3613.0	Semi standard non polar	33892256
Riboflavin,1TBDMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO)C1=NC(=O)[NH]C(=O)C1=N2	3590.3	Semi standard non polar	33892256
Riboflavin,1TBDMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3616.8	Semi standard non polar	33892256
Riboflavin,1TBDMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3613.4	Semi standard non polar	33892256
Riboflavin,1TBDMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3713.2	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO)C1=NC(=O)[NH]C(=O)C1=N2	3673.7	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #10	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3802.5	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3672.9	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3682.3	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3793.9	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3636.3	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #6	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3629.7	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #7	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3774.8	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #8	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3691.3	Semi standard non polar	33892256
Riboflavin,2TBDMS,isomer #9	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3794.4	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3762.7	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #10	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3913.2	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3745.3	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3900.6	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3775.9	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3901.6	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #6	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3907.6	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #7	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3758.6	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #8	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3878.2	Semi standard non polar	33892256
Riboflavin,3TBDMS,isomer #9	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	3867.0	Semi standard non polar	33892256
Riboflavin,4TBDMS,isomer #1	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1=NC(=O)[NH]C(=O)C1=N2	3936.4	Semi standard non polar	33892256
Riboflavin,4TBDMS,isomer #2	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	4054.2	Semi standard non polar	33892256
Riboflavin,4TBDMS,isomer #3	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	4035.6	Semi standard non polar	33892256
Riboflavin,4TBDMS,isomer #4	CC1=CC2=C(C=C1C)N(C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	4059.6	Semi standard non polar	33892256
Riboflavin,4TBDMS,isomer #5	CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1=N2	4044.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Riboflavin EI-B (Non-derivatized)	splash10-006x-4980000000-dd278a577316361d270a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Riboflavin EI-B (Non-derivatized)	splash10-006x-4980000000-dd278a577316361d270a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0btc-9014000000-75f046dc3c6cb008690e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (4 TMS) - 70eV, Positive	splash10-0zfs-5146149000-f9db57dd1ccd4a014604	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riboflavin GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0a4i-0091000000-a82c54d3153103fcdb1f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0091000000-a82c54d3153103fcdb1f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Linear Ion Trap , negative-QTOF	splash10-0a4i-0090000000-2aff124ee1fc62c13844	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Linear Ion Trap , negative-QTOF	splash10-0a4i-0090000000-f8b29c3e2c601a944a6c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Linear Ion Trap , negative-QTOF	splash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 20V, Negative-QTOF	splash10-0a4i-0090000000-5288e9226616bb75603c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 10V, Negative-QTOF	splash10-0a4i-0093000000-5999e10d04a53f4dae9b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 20V, Negative-QTOF	splash10-0a4i-0091000000-8f391045e25f26d53384	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 40V, Negative-QTOF	splash10-08fv-0290000000-b4d5f66b726c01d08c55	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 40V, Negative-QTOF	splash10-0006-4690000000-d195fd5aee22ece7f2ec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 10V, Negative-QTOF	splash10-004i-0039000000-549fbc0a59262f64680e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 10V, Negative-QTOF	splash10-0a4i-0195000000-58354696aaddaffc0fd8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 40V, Negative-QTOF	splash10-0f76-9231000000-67715e21d6e9ce2655fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 35V, Negative-QTOF	splash10-0a4i-0090000000-838afb0228d293bee0a3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 20V, Negative-QTOF	splash10-0a4i-2190000000-b659be001c9aa265c257	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin 35V, Negative-QTOF	splash10-0a4i-0090000000-21473bfb7f4a3eafd059	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-0019000000-86365dedafa031aa7787	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-4390000000-ac1b59ab7cc2209f4241	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00dj-4900000000-72d33eb27b9bd6a13d9e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-004l-0569000000-874b71fdc78d04853bf0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin LC-ESI-qTof , Positive-QTOF	splash10-004i-0239000000-659ca9fae9643f3ce73d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin LC-ESI-QTOF , positive-QTOF	splash10-004l-0569000000-874b71fdc78d04853bf0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Linear Ion Trap , positive-QTOF	splash10-0006-0092000000-1f1be5508c1d50d8dff7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Linear Ion Trap , positive-QTOF	splash10-0006-0092000000-74bf0b86efe72fe37198	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Riboflavin Linear Ion Trap , positive-QTOF	splash10-057i-0069000000-bb0522be4472e049dbc5	2017-09-14	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Erythrocyte
Heart
Kidney
Liver
Placenta
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Riboflavin Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.845 (0.361-1.77) uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.015 (0.0054-0.028) uM	Adult (>18 years old)	Both	Normal	12194936	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.385 (0.15-0.96) uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.530 (0.265-1.30) uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.10-0.50 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.00797-0.0399 uM	Adolescent (13-18 years old)	Not Specified	Normal	27702554	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.35 +/- 0.05 uM	Adult (>18 years old)	Not Specified	Normal	182198	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	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	0.710 +/- 0.180 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.754 +/- 0.222 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.880 +/- 0.375 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.058 +/- 0.048 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	0.578 +/- 0.157 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.578 +/- 0.157 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.18 +/- 0.08 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.24 +/- 0.24 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.04 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.0193 +/- 0.0139 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	20576202	details
Urine	Detected and Quantified	0.0255 +/- 0.0208 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20502474	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.015 +/- 0.018 uM	Adolescent (13-18 years old)	Female	Anorexia nervosa	10197568	details
Blood	Detected and Quantified	0.00502 uM	Adolescent (13-18 years old)	Not Available	Brown-Vialetto-Van Laere Syndrome 1	27702554	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.18 +/- 0.02 uM	Adult (>18 years old)	Not Specified	Alcoholism	182198	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.14 +/- 0.06 uM	Adult (>18 years old)	Not Specified	Alcoholism	182198	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	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Cardiosvacular risk	Mar Garcia-A...	details
Urine	Detected and Quantified	4.757 +/- 5.779 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Anorexia nervosa
Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed:10197568 ]
Brown-Vialetto-Van Laere Syndrome 1
Udhayabanu T, Subramanian VS, Teafatiller T, Gowda VK, Raghavan VS, Varalakshmi P, Said HM, Ashokkumar B: SLC52A2 [p.P141T] and SLC52A3 [p.N21S] causing Brown-Vialetto-Van Laere Syndrome in an Indian patient: First genetically proven case with mutations in two riboflavin transporters. Clin Chim Acta. 2016 Nov 1;462:210-214. doi: 10.1016/j.cca.2016.09.022. Epub 2016 Oct 1. [PubMed:27702554 ]
Alcoholism
Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. [PubMed:182198 ]
Colorectal cancer
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 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

606788 (Anorexia nervosa)
211530 (Brown-Vialetto-Van Laere Syndrome 1)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB00140

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Riboflavin

METLIN ID

Not Available

PubChem Compound

493570

PDB ID

Not Available

ChEBI ID

17015

Food Biomarker Ontology

Not Available

VMH ID

RIBFLV

MarkerDB ID

MDB00000119

Good Scents ID

Not Available

References

Synthesis Reference

Tishler, Max; Pfister, Karl, III; Babson, R. D.; Ladenburg, Kurt; Fleming, Ann J. Reaction between o-aminoazo compounds and barbituric acid. A new synthesis of riboflavin. Journal of the American Chemical Society (1947), 69 1487-92.

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 ]
Mathew JL, Kabi BC, Rath B: Anti-oxidant vitamins and steroid responsive nephrotic syndrome in Indian children. J Paediatr Child Health. 2002 Oct;38(5):450-37. [PubMed:12354259 ]
Booth CK, Clark T, Fenn A: Folic acid, riboflavin, thiamine, and vitamin B-6 status of a group of first-time blood donors. Am J Clin Nutr. 1998 Nov;68(5):1075-80. [PubMed:9808225 ]
Boisvert WA, Mendoza I, Castaneda C, De Portocarrero L, Solomons NW, Gershoff SN, Russell RM: Riboflavin requirement of healthy elderly humans and its relationship to macronutrient composition of the diet. J Nutr. 1993 May;123(5):915-25. [PubMed:8487103 ]
Mikalunas V, Fitzgerald K, Rubin H, McCarthy R, Craig RM: Abnormal vitamin levels in patients receiving home total parenteral nutrition. J Clin Gastroenterol. 2001 Nov-Dec;33(5):393-6. [PubMed:11606856 ]
Belko AZ, Obarzanek E, Roach R, Rotter M, Urban G, Weinberg S, Roe DA: Effects of aerobic exercise and weight loss on riboflavin requirements of moderately obese, marginally deficient young women. Am J Clin Nutr. 1984 Sep;40(3):553-61. [PubMed:6475825 ]
Alexander M, Emanuel G, Golin T, Pinto JT, Rivlin RS: Relation of riboflavin nutriture in healthy elderly to intake of calcium and vitamin supplements: evidence against riboflavin supplementation. Am J Clin Nutr. 1984 Apr;39(4):540-6. [PubMed:6546833 ]
Baeckert PA, Greene HL, Fritz I, Oelberg DG, Adcock EW: Vitamin concentrations in very low birth weight infants given vitamins intravenously in a lipid emulsion: measurement of vitamins A, D, and E and riboflavin. J Pediatr. 1988 Dec;113(6):1057-65. [PubMed:3142982 ]
Maiani G, Mobarhan S, Nicastro A, Virgili F, Scaccini C, Ferro-Luzzi A: [Determination of glutathione reductase activity in erythrocytes and whole blood as an indicator of riboflavin nutrition]. Acta Vitaminol Enzymol. 1983;5(3):171-8. [PubMed:6650303 ]
Bamji MS, Bhaskaram P, Jacob CM: Urinary riboflavin excretion and erythrocyte glutathione reductase activity in preschool children suffering from upper respiratory infections and measles. Ann Nutr Metab. 1987;31(3):191-6. [PubMed:3592624 ]
Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. [PubMed:2631092 ]
Kodentsova VM, Vrzhesinskaya OA, Spirichev VB: Fluorometric riboflavin titration in plasma by riboflavin-binding apoprotein as a method for vitamin B2 status assessment. Ann Nutr Metab. 1995;39(6):355-60. [PubMed:8678471 ]
Bates CJ, Powers HJ: A simple fluorimetric assay for pyridoxamine phosphate oxidase in erythrocyte haemolysates: effects of riboflavin supplementation and of glucose 6-phosphate dehydrogenase deficiency. Hum Nutr Clin Nutr. 1985 Mar;39(2):107-15. [PubMed:4019261 ]
Brun TA, Chen J, Campbell TC, Boreham J, Feng Z, Parpia B, Shen TF, Li M: Urinary riboflavin excretion after a load test in rural China as a measure of possible riboflavin deficiency. Eur J Clin Nutr. 1990 Mar;44(3):195-206. [PubMed:2369885 ]
Mulherin DM, Thurnham DI, Situnayake RD: Glutathione reductase activity, riboflavin status, and disease activity in rheumatoid arthritis. Ann Rheum Dis. 1996 Nov;55(11):837-40. [PubMed:8976642 ]
Rao PN, Levine E, Myers MO, Prakash V, Watson J, Stolier A, Kopicko JJ, Kissinger P, Raj SG, Raj MH: Elevation of serum riboflavin carrier protein in breast cancer. Cancer Epidemiol Biomarkers Prev. 1999 Nov;8(11):985-90. [PubMed:10566553 ]
Zhou X, Huang C, Hong J, Yao S: [Nested case-control study on riboflavin levels in blood and urine and the risk of lung cancer]. Wei Sheng Yan Jiu. 2003 Nov;32(6):597-8, 601. [PubMed:14963913 ]
Thurnham DI, Zheng SF, Munoz N, Crespi M, Grassi A, Hambidge KM, Chai TF: Comparison of riboflavin, vitamin A, and zinc status of Chinese populations at high and low risk for esophageal cancer. Nutr Cancer. 1985;7(3):131-43. [PubMed:3878498 ]
Bates CJ, Prentice AM, Paul AA, Prentice A, Sutcliffe BA, Whitehead RG: Riboflavin status in infants born in rural Gambia, and the effect of a weaning food supplement. Trans R Soc Trop Med Hyg. 1982;76(2):253-8. [PubMed:7101408 ]
Dror Y, Stern F, Komarnitsky M: Optimal and stable conditions for the determination of erythrocyte glutathione reductase activation coefficient to evaluate riboflavin status. Int J Vitam Nutr Res. 1994;64(4):257-62. [PubMed:7883462 ]
Switzer BR, Stark AH, Atwood JR, Ritenbaugh C, Travis RG, Wu HM: Development of a urinary riboflavin adherence marker for a wheat bran fiber community intervention trial. Cancer Epidemiol Biomarkers Prev. 1997 Jun;6(6):439-42. [PubMed:9184778 ]
Zempleni J, Galloway JR, McCormick DB: Pharmacokinetics of orally and intravenously administered riboflavin in healthy humans. Am J Clin Nutr. 1996 Jan;63(1):54-66. [PubMed:8604671 ]
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 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Lysosomal acid phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: Not Available
Gene Name:: ACP2
Uniprot ID:: P11117
Molecular weight:: 48343.92

Reactions

Flavin mononucleotide + Water → Riboflavin + Phosphate	details

Enzyme Details

2. Low molecular weight phosphotyrosine protein phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: Acts on tyrosine phosphorylated proteins, low-MW aryl phosphates and natural and synthetic acyl phosphates. Isoform 3 does not possess phosphatase activity.
Gene Name:: ACP1
Uniprot ID:: P24666
Molecular weight:: 18042.315

Reactions

Flavin mononucleotide + Water → Riboflavin + Phosphate	details

Enzyme Details

3. Tartrate-resistant acid phosphatase type 5

General function:: Involved in hydrolase activity
Specific function:: Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:: ACP5
Uniprot ID:: P13686
Molecular weight:: 36598.47

Reactions

Flavin mononucleotide + Water → Riboflavin + Phosphate	details

Enzyme Details

4. Prostatic acid phosphatase

General function:: Involved in acid phosphatase activity
Specific function:: A non-specific tyrosine phosphatase that dephosphorylates a diverse number of substrates under acidic conditions (pH 4-6) including alkyl, aryl, and acyl orthophosphate monoesters and phosphorylated proteins. Has lipid phosphatase activity and inactivates lysophosphatidic acid in seminal plasma. Isoform 2: the cellular form also has ecto-5'-nucleotidase activity in dorsal root ganglion (DRG) neurons. Generates adenosine from AMP which acts as a pain suppressor. Acts as a tumor suppressor of prostate cancer through dephosphorylation of ERBB2 and deactivation of MAPK-mediated signaling.
Gene Name:: ACPP
Uniprot ID:: P15309
Molecular weight:: 44565.715

Reactions

Flavin mononucleotide + Water → Riboflavin + Phosphate	details

Enzyme Details

5. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

References

Strolin Benedetti M, Tipton KF, Whomsley R: Amine oxidases and monooxygenases in the in vivo metabolism of xenobiotic amines in humans: has the involvement of amine oxidases been neglected? Fundam Clin Pharmacol. 2007 Oct;21(5):467-80. [PubMed:17868200 ]

Enzyme Details

6. Methylenetetrahydrofolate reductase

General function:: Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:: Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:: MTHFR
Uniprot ID:: P42898
Molecular weight:: 74595.895

References

Bates CJ, Fuller NJ: The effect of riboflavin deficiency on methylenetetrahydrofolate reductase (NADPH) (EC 1.5.1.20) and folate metabolism in the rat. Br J Nutr. 1986 Mar;55(2):455-64. [PubMed:3676170 ]
Macdonald HM, McGuigan FE, Fraser WD, New SA, Ralston SH, Reid DM: Methylenetetrahydrofolate reductase polymorphism interacts with riboflavin intake to influence bone mineral density. Bone. 2004 Oct;35(4):957-64. [PubMed:15454103 ]

Enzyme Details

7. Glycogen phosphorylase, liver form

General function:: Involved in phosphorylase activity
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:: PYGL
Uniprot ID:: P06737
Molecular weight:: 93133.25

Enzyme Details

8. Flavin reductase (NADPH)

General function:: Involved in catalytic activity
Specific function:: Broad specificity oxidoreductase that catalyzes the NADPH-dependent reduction of a variety of flavins, such as riboflavin, FAD or FMN, biliverdins, methemoglobin and PQQ (pyrroloquinoline quinone). Contributes to heme catabolism and metabolizes linear tetrapyrroles. Can also reduce the complexed Fe(3+) iron to Fe(2+) in the presence of FMN and NADPH. In the liver, converts biliverdin to bilirubin.
Gene Name:: BLVRB
Uniprot ID:: P30043
Molecular weight:: 22119.215

Reactions

Riboflavin reduced + NADP → Riboflavin + NADPH	details
Riboflavin reduced + NADP → Riboflavin + NADPH + Hydrogen Ion	details

References

Russell TR, Demeler B, Tu SC: Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin. Biochemistry. 2004 Feb 17;43(6):1580-90. [PubMed:14769034 ]
van Pee KH, Patallo EP: Flavin-dependent halogenases involved in secondary metabolism in bacteria. Appl Microbiol Biotechnol. 2006 May;70(6):631-41. Epub 2006 Mar 17. [PubMed:16544142 ]

Enzyme Details

9. Riboflavin kinase

General function:: Involved in riboflavin kinase activity
Specific function:: Catalyzes the phosphorylation of riboflavin (vitamin B2) to form flavin-mononucleotide (FMN).
Gene Name:: RFK
Uniprot ID:: Q969G6
Molecular weight:: 17623.08

Reactions

Adenosine triphosphate + Riboflavin → ADP + Flavin mononucleotide	details

References

Werner R, Manthey KC, Griffin JB, Zempleni J: HepG2 cells develop signs of riboflavin deficiency within 4 days of culture in riboflavin-deficient medium. J Nutr Biochem. 2005 Oct;16(10):617-24. [PubMed:16081269 ]
Solovieva IM, Kreneva RA, Errais Lopes L, Perumov DA: The riboflavin kinase encoding gene ribR of Bacillus subtilis is a part of a 10 kb operon, which is negatively regulated by the yrzC gene product. FEMS Microbiol Lett. 2005 Feb 1;243(1):51-8. [PubMed:15668000 ]
Ishchuk OP, Iatsyshyn VIu, Dmytruk KV, Voronovs'kyi AIa, Fedorovych DV, Sybirnyi AA: [Construction of the flavinogenic yeast Candida famata strains with high riboflavin kinase activity using gene engineering]. Ukr Biokhim Zh (1999). 2006 Sep-Oct;78(5):63-9. [PubMed:17290783 ]
Sandoval FJ, Roje S: An FMN hydrolase is fused to a riboflavin kinase homolog in plants. J Biol Chem. 2005 Nov 18;280(46):38337-45. Epub 2005 Sep 23. [PubMed:16183635 ]
Bertollo CM, Oliveira AC, Rocha LT, Costa KA, Nascimento EB Jr, Coelho MM: Characterization of the antinociceptive and anti-inflammatory activities of riboflavin in different experimental models. Eur J Pharmacol. 2006 Oct 10;547(1-3):184-91. Epub 2006 Jul 26. [PubMed:16962092 ]
Hirano G, Izumi H, Yasuniwa Y, Shimajiri S, Ke-Yong W, Sasagiri Y, Kusaba H, Matsumoto K, Hasegawa T, Akimoto M, Akashi K, Kohno K: Involvement of riboflavin kinase expression in cellular sensitivity against cisplatin. Int J Oncol. 2011 Apr;38(4):893-902. doi: 10.3892/ijo.2011.938. Epub 2011 Feb 9. [PubMed:21308351 ]

Enzyme Details

10. Solute carrier family 52, riboflavin transporter, member 1

General function:: Involved in receptor activity
Specific function:: Riboflavin transporter. Riboflavin transport is Na(+)-independent but moderately pH-sensitive. Activity is strongly inhibited by riboflavin analogs, such as lumiflavin. Weakly inhibited by flavin adenine dinucleotide (FAD). In case of infection by retroviruses, acts as a cell receptor to retroviral envelopes similar to the porcine endogenous retrovirus (PERV-A).
Gene Name:: SLC52A1
Uniprot ID:: Q9NWF4
Molecular weight:: 46316.245

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for Riboflavin (HMDB0000244)

MOL for HMDB0000244 (Riboflavin)

3D MOL for HMDB0000244 (Riboflavin)

3D SDF for HMDB0000244 (Riboflavin)

3D-SDF for HMDB0000244 (Riboflavin)

PDB for HMDB0000244 (Riboflavin)

3D PDB for HMDB0000244 (Riboflavin)

SMILES for HMDB0000244 (Riboflavin)

INCHI for HMDB0000244 (Riboflavin)

Structure for HMDB0000244 (Riboflavin)

3D Structure for HMDB0000244 (Riboflavin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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References

References

Reactions

References

Reactions

References

Transporters

References