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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:45:30 UTC

HMDB ID

HMDB0001491

Secondary Accession Numbers

HMDB01491

Metabolite Identification

Common Name

Pyridoxal 5'-phosphate

Description

Pyridoxal phosphate, also known as PLP, pyridoxal 5'-phosphate or P5P, is the active form of vitamin B6. It is a coenzyme in a variety of enzymatic reactions. Pyridoxal 5'-phosphate belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal 5'-phosphate is a drug which is used for nutritional supplementation and for treating dietary shortage or imbalance. Pyridoxal 5'-phosphate exists in all living species, ranging from bacteria to humans. In humans, pyridoxal 5'-phosphate is involved in glycine and serine metabolism. Outside of the human body, pyridoxal 5'-phosphate is found, on average, in the highest concentration within cow milk. Pyridoxal 5'-phosphate has also been detected, but not quantified in several different foods, such as soursops, italian sweet red peppers, muscadine grapes, european plums, and blackcurrants. Pyridoxal 5'-phosphate, with regard to humans, has been found to be associated with several diseases such as epilepsy, early-onset, vitamin B6-dependent, odontohypophosphatasia, pyridoxamine 5-prime-phosphate oxidase deficiency, and hypophosphatasia. Pyridoxal 5'-phosphate has also been linked to the inborn metabolic disorder celiac disease.

Structure

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

114
  Mrv1652309042000232D          

 16 16  0  0  0  0            999 V2000
    6.3799    0.2063    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7925   -0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9674    0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  1  7  2  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  0  0  0  0
  6 16  2  0  0  0  0
  8 13  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  2  0  0  0  0
 10 12  2  0  0  0  0
 10 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001491

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)

> <INCHI_KEY>
NGVDGCNFYWLIFO-UHFFFAOYSA-N

> <FORMULA>
C8H10NO6P

> <MOLECULAR_WEIGHT>
247.1419

> <EXACT_MASS>
247.024573569

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.898887181263255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
-2.0856087036128135

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.691277029499376

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.680298610655746

> <JCHEM_PKA_STRONGEST_BASIC>
4.109012435085948

> <JCHEM_POLAR_SURFACE_AREA>
116.95

> <JCHEM_REFRACTIVITY>
54.746300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyridoxal phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 114                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  P   UNK     0      11.909   0.385   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      10.576  -0.385   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907   0.385   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.679  -0.949   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.243   1.155   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.241   2.695   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      11.139   1.719   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       6.574  -2.695   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.908  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.242   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.241  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908  -1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.907  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574   1.925   0.000  0.00  0.00           C+0
CONECT    1    2    4    5    7                                             
CONECT    2    1   11                                                       
CONECT    3   12                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6   16                                                            
CONECT    7    1                                                            
CONECT    8   13   14                                                       
CONECT    9   10   11   14                                                  
CONECT   10    9   12   16                                                  
CONECT   11    2    9                                                       
CONECT   12    3   10   13                                                  
CONECT   13    8   12   15                                                  
CONECT   14    8    9                                                       
CONECT   15   13                                                            
CONECT   16    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001491
HETATM    1  C1  UNL     1      -3.905  -1.496  -0.335  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.504  -0.954  -0.225  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.485  -1.803  -0.095  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.231  -1.333   0.004  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.077   0.014  -0.021  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.486   0.494   0.092  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.302  -0.608   0.214  1.00  0.00           O  
HETATM    8  P1  UNL     1       3.924  -0.235   0.351  1.00  0.00           P  
HETATM    9  O2  UNL     1       4.217   0.086   1.809  1.00  0.00           O  
HETATM   10  O3  UNL     1       4.824  -1.605  -0.104  1.00  0.00           O  
HETATM   11  O4  UNL     1       4.386   1.060  -0.624  1.00  0.00           O  
HETATM   12  C6  UNL     1      -0.983   0.887  -0.156  1.00  0.00           C  
HETATM   13  C7  UNL     1      -0.719   2.303  -0.188  1.00  0.00           C  
HETATM   14  O5  UNL     1      -1.699   3.114  -0.313  1.00  0.00           O  
HETATM   15  C8  UNL     1      -2.258   0.392  -0.256  1.00  0.00           C  
HETATM   16  O6  UNL     1      -3.339   1.275  -0.393  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.200  -1.427  -1.410  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.897  -2.572  -0.072  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.593  -0.928   0.328  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.623  -2.006   0.112  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.762   1.147  -0.760  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.528   1.117   1.020  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.274  -2.424   0.018  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.437   1.870  -0.046  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.259   2.708  -0.113  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.285   0.924  -0.468  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   15
CONECT    3    4
CONECT    4    5    5   20
CONECT    5    6   12
CONECT    6    7   21   22
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   23
CONECT   11   24
CONECT   12   13   15   15
CONECT   13   14   14   25
CONECT   15   16
CONECT   16   26
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate	ChEBI
Codecarboxylase	ChEBI
Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester	ChEBI
PLP	ChEBI
Pyridoxal 5'-(dihydrogen phosphate)	ChEBI
Pyridoxal 5-monophosphoric acid ester	ChEBI
Pyridoxal 5-phosphate	ChEBI
Pyridoxal phosphate	ChEBI
PYRIDOXAL-5'-phosphATE	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid	Generator
Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester	Generator
Pyridoxal 5'-(dihydrogen phosphoric acid)	Generator
Pyridoxal 5-monophosphate ester	Generator
Pyridoxal 5-phosphoric acid	Generator
Pyridoxal phosphoric acid	Generator
PYRIDOXAL-5'-phosphoric acid	Generator
Pyridoxal 5'-phosphoric acid	Generator
Apolon b6	HMDB
Biosechs	HMDB
Coenzyme b6	HMDB
Hairoxal	HMDB
Hexermin-p	HMDB
Hi-pyridoxin	HMDB
Hiadelon	HMDB
Himitan	HMDB
PAL-p	HMDB
Phosphopyridoxal	HMDB
Phosphopyridoxal coenzyme	HMDB
Pidopidon	HMDB
Piodel	HMDB
Pydoxal	HMDB
Pyridoxal p	HMDB
Pyridoxal-p	HMDB
Pyridoxyl phosphate	HMDB
Pyromijin	HMDB
Sechvitan	HMDB
Vitahexin-p	HMDB
Vitazechs	HMDB
Phosphate, pyridoxal	HMDB
Pyridoxal 5 phosphate	HMDB

Chemical Formula

C₈H₁₀NO₆P

Average Molecular Weight

247.1419

Monoisotopic Molecular Weight

247.024573569

IUPAC Name

[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid

Traditional Name

pyridoxal phosphate

CAS Registry Number

54-47-7

SMILES

CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O

InChI Identifier

InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)

InChI Key

NGVDGCNFYWLIFO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridine carboxaldehydes

Direct Parent

Pyridoxals and derivatives

Alternative Parents

Substituents

Pyridoxal
Aryl-aldehyde
Monoalkyl phosphate
Hydroxypyridine
Methylpyridine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Vinylogous acid
Heteroaromatic compound
Azacycle
Organopnictogen compound
Aldehyde
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:18405 )
pyridinecarbaldehyde (CHEBI:18405 )
methylpyridines (CHEBI:18405 )
vitamin B6 phosphate (CHEBI:18405 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16277678)
Cerebrospinal Fluid (CSF) (PMID: 6182788)
Cerebrospinal fluid (HMDB: HMDB0001491)

Tissue substructure

Muscle (HMDB: HMDB0001491)

Cell

Organ

Kidney (HMDB: HMDB0001491)
Liver (HMDB: HMDB0001491)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0001491)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001491)

Membrane (HMDB: HMDB0001491)
Cytoplasm (HMDB: HMDB0001491)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001491)

Source

Endogenous

Endogenous (HMDB: HMDB0001491)

Plant

Animal

Animal (HMDB: HMDB0001491)

Exogenous

Food

Food (HMDB: HMDB0001491)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Glucose-Alanine Cycle (HMDB: HMDB0001491)
Vitamin B6 Metabolism (HMDB: HMDB0001491)
Malate-Aspartate Shuttle (HMDB: HMDB0001491)
Alanine Metabolism (HMDB: HMDB0001491)
Porphyrin Metabolism (PathBank: SMP0000953)
Sphingolipid Metabolism (PathBank: SMP0002378)
Sulfur Metabolism (PathBank: SMP0002382)
Arginine and Proline Metabolism (PathBank: SMP0012004)
Vitamin B6 Metabolism (PathBank: SMP0063472)
Ammonia Recycling (PathBank: SMP0063579)
Alanine Metabolism (PathBank: SMP0063586)
Selenoamino Acid Metabolism (PathBank: SMP0063587)
Cysteine Metabolism (PathBank: SMP0063607)
Histidine Metabolism (PathBank: SMP0063632)
Methionine Metabolism (PathBank: SMP0063637)
Sphingolipid Metabolism (PathBank: SMP0063667)
Spermidine and Spermine Biosynthesis (PathBank: SMP0063671)
Beta-Alanine metabolism (PathBank: SMP0087180)
Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z)) (PathBank: SMP0071724)
Phosphatidylethanolamine Biosynthesis PE(16:0/20:0) (PathBank: SMP0071727)
Phosphatidylethanolamine Biosynthesis PE(16:0/22:0) (PathBank: SMP0071730)
Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z)) (PathBank: SMP0071739)
Phosphatidylethanolamine Biosynthesis PE(18:0/22:0) (PathBank: SMP0071741)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z)) (PathBank: SMP0071743)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z)) (PathBank: SMP0071769)
Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071771)
Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0) (PathBank: SMP0071772)
Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z)) (PathBank: SMP0071788)
Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z)) (PathBank: SMP0071791)
Urea Cycle (PathBank: SMP0087224)
Threonine and 2-Oxobutanoate Degradation (PathBank: SMP0087262)
Glutamate Metabolism (PathBank: SMP0087278)
Homocysteine Degradation (PathBank: SMP0087298)
Tyrosine Metabolism (PathBank: SMP0087328)
Aspartate Metabolism (PathBank: SMP0087369)
Glycine and Serine Metabolism (PathBank: SMP0087466)
Propanoate Metabolism (PathBank: SMP0087480)
Sulfur Metabolism (Ethanesulfonate) (PathBank: SMP0121318)
Starch and Sucrose Metabolism (PathBank: SMP0000958)
Taurine and Hypotaurine Metabolism (PathBank: SMP0063675)
Valine, Leucine, and Isoleucine Degradation (PathBank: SMP0063689)
Tryptophan Metabolism (PathBank: SMP0063693)
Phosphatidylethanolamine Biosynthesis PE(16:0/18:0) (PathBank: SMP0071721)
Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0071725)
Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z)) (PathBank: SMP0071728)
Phosphatidylethanolamine Biosynthesis PE(18:0/18:0) (PathBank: SMP0071732)
Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0071736)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0071746)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z)) (PathBank: SMP0071749)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z)) (PathBank: SMP0071752)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0071754)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071764)
Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0071770)
Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z)) (PathBank: SMP0071773)
Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z)) (PathBank: SMP0071776)
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071777)
Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z)) (PathBank: SMP0071787)
Phosphatidylethanolamine Biosynthesis PE(22:0/22:0) (PathBank: SMP0071795)
Lysine Degradation (PathBank: SMP0087300)
Phenylalanine and Tyrosine Metabolism (PathBank: SMP0087313)
Folate Metabolism (PathBank: SMP0087435)
Cysteine Biosynthesis (PathBank: SMP0121282)
Porphyrin Metabolism (PathBank: SMP0002363)
Starch and Sucrose Metabolism (PathBank: SMP0002380)
Phosphatidylethanolamine Biosynthesis PE(16:0/16:0) (PathBank: SMP0071720)
Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z)) (PathBank: SMP0071723)
Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z)) (PathBank: SMP0071731)
Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z)) (PathBank: SMP0071733)
Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z)) (PathBank: SMP0071734)
Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z)) (PathBank: SMP0071735)
Phosphatidylethanolamine Biosynthesis PE(18:0/20:0) (PathBank: SMP0071738)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0) (PathBank: SMP0071748)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0) (PathBank: SMP0071751)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071756)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0) (PathBank: SMP0071757)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z)) (PathBank: SMP0071758)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0) (PathBank: SMP0071760)
Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0) (PathBank: SMP0071775)
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0) (PathBank: SMP0071778)
Phosphatidylethanolamine Biosynthesis PE(20:0/20:0) (PathBank: SMP0071783)
Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z)) (PathBank: SMP0071796)
Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z)) (PathBank: SMP0071797)
Carnitine Synthesis (PathBank: SMP0087187)
Sulfur Metabolism (Butanesulfonate) (PathBank: SMP0121316)
Sulfur Metabolism (Isethionate) (PathBank: SMP0121319)
Secondary Metabolites: Trehalose Biosynthesis and Metabolism (PathBank: SMP0121327)
Phosphatidylcholine Biosynthesis (PathBank: SMP0014205)
Catecholamine Biosynthesis (PathBank: SMP0063606)
Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z)) (PathBank: SMP0071722)
Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0071726)
Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0071737)
Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z)) (PathBank: SMP0071742)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(11Z)) (PathBank: SMP0071744)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0071745)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0071747)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z)) (PathBank: SMP0071753)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0071755)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z)) (PathBank: SMP0071761)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0071762)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0071763)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0) (PathBank: SMP0071765)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z)) (PathBank: SMP0071766)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0) (PathBank: SMP0071768)
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0071779)
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0) (PathBank: SMP0071781)
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0071782)
Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z)) (PathBank: SMP0071784)
Phosphatidylethanolamine Biosynthesis PE(20:0/22:0) (PathBank: SMP0071786)
Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0) (PathBank: SMP0071790)
Threonine Biosynthesis (PathBank: SMP0121292)
Sulfur Metabolism (Propanesulfonate) (PathBank: SMP0121317)
Sulfur Metabolism (Methanesulfonate) (PathBank: SMP0121320)
Phenylalanine Metabolism (PathBank: SMP0000938)
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis (PathBank: SMP0000975)
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 2 (PathBank: SMP0002059)
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 3 (PathBank: SMP0002060)
Vitamin B6 (PathBank: SMP0002387)
Choline Biosynthesis I (PathBank: SMP0012026)
Choline Biosynthesis II (PathBank: SMP0012027)
Plastoquinol-9 Biosynthesis (PathBank: SMP0012043)
Thio-Molybdenum Cofactor Biosynthesis (PathBank: SMP0012046)
Glycine Betaine Biosynthesis I (PathBank: SMP0012047)
Glycine Betaine Biosynthesis II (PathBank: SMP0012048)
Butanoate metabolism (PathBank: SMP0012467)
Phosphatidylethanolamine Biosynthesis (PathBank: SMP0014208)
Isoquinoline Alkaloid Biosynthesis (PathBank: SMP0063471)
Tropane, Piperidine, and Pyridine Alkaloid Biosynthesis (PathBank: SMP0063474)
Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(13Z)) (PathBank: SMP0071729)
Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(13Z)) (PathBank: SMP0071740)
Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(13Z)) (PathBank: SMP0071750)
Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(13Z)) (PathBank: SMP0071759)
Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(13Z)) (PathBank: SMP0071767)
Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(13Z)) (PathBank: SMP0071774)
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(13Z)) (PathBank: SMP0071780)
Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(13Z)) (PathBank: SMP0071785)
Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(13Z)) (PathBank: SMP0071789)
Phosphatidylethanolamine Biosynthesis PE(20:1(13Z)/20:1(13Z)) (PathBank: SMP0071792)
Phosphatidylethanolamine Biosynthesis PE(20:1(13Z)/22:0) (PathBank: SMP0071793)
Phosphatidylethanolamine Biosynthesis PE(20:1(13Z)/22:1(13Z)) (PathBank: SMP0071794)
L-Homomethionine Biosynthesis (PathBank: SMP0121204)

Disease pathway

Hypophosphatasia (HMDB: HMDB0001491)
Cystinosis, Ocular Nonnephropathic (HMDB: HMDB0001491)
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD) (PathBank: SMP0000340)
Glutaminolysis and Cancer (PathBank: SMP0108773)
Sarcosine Oncometabolite Pathway (PathBank: SMP0108776)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120445)
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency) (PathBank: SMP0120454)
Cystathionine beta-Synthase Deficiency (PathBank: SMP0120471)
GABA-Transaminase Deficiency (PathBank: SMP0120478)
Hereditary Coproporphyria (HCP) (PathBank: SMP0120492)
Histidinemia (PathBank: SMP0120493)
Hypermethioninemia (PathBank: SMP0120498)
Sarcosinemia (PathBank: SMP0120521)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120523)
Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency (PathBank: SMP0120569)
Isovaleric Acidemia (PathBank: SMP0120589)
Glycogenosis, Type III. Cori Disease, Debrancher Glycogenosis (PathBank: SMP0120617)
Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120631)
Pyridoxine Dependency with Seizures (PathBank: SMP0120635)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0120663)
Argininemia (PathBank: SMP0120676)
Argininosuccinic Aciduria (PathBank: SMP0120677)
Beta-Ketothiolase Deficiency (PathBank: SMP0120679)
Canavan Disease (PathBank: SMP0120681)
Carbamoyl Phosphate Synthetase Deficiency (PathBank: SMP0120682)
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease (PathBank: SMP0120689)
Dihydropyrimidine Dehydrogenase Deficiency (DHPD) (PathBank: SMP0120694)
Globoid Cell Leukodystrophy (PathBank: SMP0120702)
Glutaric Aciduria Type I (PathBank: SMP0120704)
Glycine N-Methyltransferase Deficiency (PathBank: SMP0120707)
Hyperprolinemia Type I (PathBank: SMP0120719)
Hypoacetylaspartia (PathBank: SMP0120722)
Tyrosinemia Type 3 (TYRO3) (PathBank: SMP0120731)
Metachromatic Leukodystrophy (MLD) (PathBank: SMP0120738)
Methionine Adenosyltransferase Deficiency (PathBank: SMP0120739)
Ornithine Transcarbamylase Deficiency (OTC Deficiency) (PathBank: SMP0120762)
Porphyria Variegata (PV) (PathBank: SMP0120764)
Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Beta-Mercaptolactate-Cysteine Disulfiduria (PathBank: SMP0120783)
Hyperornithinemia with Gyrate Atrophy (HOGA) (PathBank: SMP0120789)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0120806)
Mucopolysaccharidosis VII. Sly Syndrome (PathBank: SMP0120839)
Sucrase-Isomaltase Deficiency (PathBank: SMP0120840)
Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation Type (PathBank: SMP0120853)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0120441)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0120444)
Aromatic L-Aminoacid Decarboxylase Deficiency (PathBank: SMP0120457)
Hyperprolinemia Type II (PathBank: SMP0120501)
Tyrosinemia Type 2 (or Richner-Hanhart Syndrome) (PathBank: SMP0120513)
Methylmalonic Aciduria (PathBank: SMP0120525)
Non-Ketotic Hyperglycinemia (PathBank: SMP0120534)
Pyruvate Carboxylase Deficiency (PathBank: SMP0120535)
Prolinemia Type II (PathBank: SMP0120539)
Phenylketonuria (PathBank: SMP0120540)
Prolidase Deficiency (PD) (PathBank: SMP0120541)
Primary Hyperoxaluria Type I (PathBank: SMP0120543)
Carnosinuria, Carnosinemia (PathBank: SMP0120558)
Tyrosine Hydroxylase Deficiency (PathBank: SMP0120562)
L-Arginine:Glycine Amidinotransferase Deficiency (PathBank: SMP0120572)
Glycogen Synthetase Deficiency (PathBank: SMP0120616)
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (PathBank: SMP0120661)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0120664)
Hawkinsinuria (PathBank: SMP0120711)
Lactic Acidemia (PathBank: SMP0120724)
Tyrosinemia Type I (PathBank: SMP0120729)
Methylmalonic Aciduria Due to Cobalamin-Related Disorders (PathBank: SMP0120748)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0120790)
Gamma-Cystathionase Deficiency (CTH) (PathBank: SMP0120798)
Krabbe Disease (PathBank: SMP0120810)
Hyperlysinemia I, Familial (PathBank: SMP0120811)
Hyperlysinemia II or Saccharopinuria (PathBank: SMP0120812)
Glycogenosis, Type VI. Hers Disease (PathBank: SMP0120838)
2-Aminoadipic 2-Oxoadipic Aciduria (PathBank: SMP0120870)
3-Phosphoglycerate Dehydrogenase Deficiency (PathBank: SMP0120872)
Gaucher Disease (PathBank: SMP0120481)
Homocarnosinosis (PathBank: SMP0120494)
Maple Syrup Urine Disease (PathBank: SMP0120516)
Acute Intermittent Porphyria (PathBank: SMP0120447)
Alkaptonuria (PathBank: SMP0120453)
Citrullinemia Type I (PathBank: SMP0120466)
Propionic Acidemia (PathBank: SMP0120537)
Ornithine Aminotransferase Deficiency (OAT Deficiency) (PathBank: SMP0120538)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120588)
2-Hydroxyglutric Aciduria (D and L Form) (PathBank: SMP0120659)
Dimethylglycine Dehydrogenase Deficiency (PathBank: SMP0120695)
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) (PathBank: SMP0120710)
Isovaleric Aciduria (PathBank: SMP0120723)
Malonic Aciduria (PathBank: SMP0120734)
Saccharopinuria/Hyperlysinemia II (PathBank: SMP0120746)
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency (PathBank: SMP0120747)
Hyperglycinemia, Non-Ketotic (PathBank: SMP0120770)
Malonyl-CoA Decarboxylase Deficiency (PathBank: SMP0120786)
Fabry Disease (PathBank: SMP0120809)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)
Glycogenosis, Type IV. Amylopectinosis, Anderson Disease (PathBank: SMP0120837)
Hyperinsulinism-Hyperammonemia Syndrome (PathBank: SMP0120496)
Homocystinuria, Cystathionine beta-Synthase Deficiency (PathBank: SMP0120580)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0120586)
Cystinosis, Ocular Nonnephropathic (PathBank: SMP0120654)
Folate Malabsorption, Hereditary (PathBank: SMP0120656)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0000506)

Drug action pathway

Methotrexate Action Pathway (HMDB: HMDB0001491)
Methotrexate Action Pathway (PathBank: SMP0000432)
Disulfiram Action Pathway (PathBank: SMP0000429)

Rheumatoid arthritis (HMDB: HMDB0001491)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001491)

Biomarker

Rheumatoid arthritis (MarkerDB: MDB00000331)
Celiac disease (MarkerDB: MDB00000331)
Epilepsy (MarkerDB: MDB00000331)
Purine nucleoside phosphorylase deficiency (MarkerDB: MDB00000331)

Biological role

Human metabolite (HMDB: HMDB0001491)
Escherichia coli metabolite (HMDB: HMDB0001491)
Saccharomyces cerevisiae metabolite (HMDB: HMDB0001491)
Coenzyme (HMDB: HMDB0001491)

Modulator

Inhibitor

EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor (HMDB: HMDB0001491)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	255 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	28 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	150.538	30932474
[M-H]-	MetCCS_train_neg	146.336	30932474
[M+H]+	Baker	154.761	30932474
[M+H]+	MetCCS_train_pos	151.404	30932474
[M-H]-	Not Available	148.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000339
[M+H]+	Not Available	152.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000339

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.7 g/L	ALOGPS
logP	-0.55	ALOGPS
logP	-2.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.68	ChemAxon
pKa (Strongest Basic)	4.11	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.95 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.75 m³·mol⁻¹	ChemAxon
Polarizability	20.9 Å³	ChemAxon
Number of Rings	1	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]+	152.849	31661259
DarkChem	[M-H]-	149.58	31661259
AllCCS	[M+H]+	152.941	32859911
AllCCS	[M-H]-	147.71	32859911
DeepCCS	[M+H]+	147.643	30932474
DeepCCS	[M-H]-	145.285	30932474
DeepCCS	[M-2H]-	179.615	30932474
DeepCCS	[M+Na]+	154.766	30932474
AllCCS	[M+H]+	152.9	32859911
AllCCS	[M+H-H2O]+	149.2	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.4	32859911
AllCCS	[M-H]-	147.7	32859911
AllCCS	[M+Na-2H]-	148.1	32859911
AllCCS	[M+HCOO]-	148.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyridoxal 5'-phosphate	CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O	2937.5	Standard polar	33892256
Pyridoxal 5'-phosphate	CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O	1916.5	Standard non polar	33892256
Pyridoxal 5'-phosphate	CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O	2191.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pyridoxal 5'-phosphate,1TMS,isomer #1	CC1=NC=C(COP(=O)(O)O)C(C=O)=C1O[Si](C)(C)C	2203.8	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,1TMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O	2183.0	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,2TMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C	2256.0	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,2TMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C	2134.1	Standard non polar	33892256
Pyridoxal 5'-phosphate,2TMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C	2835.0	Standard polar	33892256
Pyridoxal 5'-phosphate,2TMS,isomer #2	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O	2195.9	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,2TMS,isomer #2	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O	2144.7	Standard non polar	33892256
Pyridoxal 5'-phosphate,2TMS,isomer #2	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O	2744.2	Standard polar	33892256
Pyridoxal 5'-phosphate,3TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C	2270.7	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,3TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C	2215.1	Standard non polar	33892256
Pyridoxal 5'-phosphate,3TMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C	2487.5	Standard polar	33892256
Pyridoxal 5'-phosphate,1TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O)C(C=O)=C1O[Si](C)(C)C(C)(C)C	2478.3	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,1TBDMS,isomer #2	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O	2420.3	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C	2696.5	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C	2562.4	Standard non polar	33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #1	CC1=NC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C	3020.2	Standard polar	33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #2	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O	2643.7	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #2	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O	2552.0	Standard non polar	33892256
Pyridoxal 5'-phosphate,2TBDMS,isomer #2	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O	2949.6	Standard polar	33892256
Pyridoxal 5'-phosphate,3TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C	2891.0	Semi standard non polar	33892256
Pyridoxal 5'-phosphate,3TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C	2755.5	Standard non polar	33892256
Pyridoxal 5'-phosphate,3TBDMS,isomer #1	CC1=NC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C	2790.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (1 MEOX; 3 TMS)	splash10-0gb9-2690000000-c9bacb7e657461e28407	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (Non-derivatized)	splash10-0gb9-2690000000-c9bacb7e657461e28407	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyridoxal 5'-phosphate GC-EI-TOF (Non-derivatized)	splash10-004j-0910000000-0408f3957221fc9882cd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Pyridoxal 5'-phosphate GC-EI-TOF (Non-derivatized)	splash10-0gb9-1790000000-b01115fa8b4cfd3612c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9520000000-bfd574b2e5355694902a	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9152000000-26c9f631195663322986	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pyridoxal 5'-phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcf	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0fxx-8900000000-ee972556340c61650528	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014l-9100000000-3cc29fb51820adecd59c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0002-0090000000-9b86e80a9dd0de14ab59	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-03dj-9800000000-9313aa9cbf19bc6311c5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0002-9500000000-7ce120a58879e2214ce5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004j-9200000000-7e6bd8c298613e59fb5d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-9000000000-4c05178b1645bf01f3fa	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0udi-3920000000-6c5e6106f5658d1d6c50	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0udi-3920000000-f96097815e6922356131	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-002b-9000000000-2c4e243699a95e3a0f88	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-002b-9000000000-8aa111485891af9f0d02	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOF	splash10-0002-0090000000-9b86e80a9dd0de14ab59	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOF	splash10-03dj-9800000000-9313aa9cbf19bc6311c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOF	splash10-0002-9500000000-7ce120a58879e2214ce5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOF	splash10-004j-9200000000-7e6bd8c298613e59fb5d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-4c05178b1645bf01f3fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF , negative-QTOF	splash10-002b-9000000000-2c4e243699a95e3a0f88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pyridoxal 5'-phosphate LC-ESI-QTOF , negative-QTOF	splash10-002b-9000000000-8aa111485891af9f0d02	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 10V, Positive-QTOF	splash10-0f6t-1790000000-1dcb07cd1110c71f7005	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 20V, Positive-QTOF	splash10-0udi-0900000000-ca6aab7f31a36863a417	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 40V, Positive-QTOF	splash10-0udi-9800000000-053802b9c0533d7943ea	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 10V, Negative-QTOF	splash10-0002-9080000000-12ca63d34d39d59f6b42	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 20V, Negative-QTOF	splash10-004i-9000000000-144099ec201adbbc4684	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyridoxal 5'-phosphate 40V, Negative-QTOF	splash10-004i-9000000000-70a9559d65e78c488e7e	2015-05-27	Wishart Lab	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

Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Erythrocyte
Kidney
Liver
Neuron
Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Glucose-Alanine Cycle		Not Available
Malate-Aspartate Shuttle		Not Available
Vitamin B6 Metabolism
Alanine, aspartate and glutamate metabolism	Not Available
Primary Hyperoxaluria Type I		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0146-0.0728 uM	Children (1-13 years old)	Not Specified	Normal	23093139	details
Blood	Detected and Quantified	0.046 (0.035-0.06) uM	Adult (>18 years old)	Both	Normal	16277678	details
Blood	Detected and Quantified	0.042 (0.0076-1.26) uM	Adult (>18 years old)	Both	Normal	15450810	details
Blood	Detected and Quantified	0.0572 +/- 0.0193 uM	Adolescent (13-18 years old)	Female	Normal	17349090	details
Blood	Detected and Quantified	0.0581 +/- 0.0176 uM	Adolescent (13-18 years old)	Male	Normal	17349090	details
Blood	Detected and Quantified	0.205 +/- 0.193 uM	Adult (>18 years old)	Male	Normal	21346713	details
Blood	Detected and Quantified	0.030 uM	Adult (>18 years old)	Female	Normal	18230968	details
Blood	Detected and Quantified	0.061 +/- 0.052 uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.056 +/- 0.042 uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.068 +/- 0.015 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.075 +/- 0.022 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0451 (0.00400-0.207) uM	Adult (>18 years old)	Both	Normal	2079838	details
Blood	Detected and Quantified	0.0047 +/- 0.00072 uM	Adult (>18 years old)	Both	Normal	1783639	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0110-0.0340 uM	Children (1-13 years old)	Not Specified	Normal	27912044	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0515 +/- 0.0166 uM	Newborn (0-30 days old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0431 +/- 0.0193 uM	Infant (0-1 year old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0305 +/- 0.0111 uM	Children (1-13 years old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0207 +/- 0.0069 uM	Children (1-13 years old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0654 +/- 0.0173 uM	Infant (0-1 year old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0531 +/- 0.0186 uM	Infant (0-1 year old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0312 +/- 0.0049 uM	Children (1-13 years old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.032-0.078 uM	Children (1-13 years old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.044-0.089 uM	Children (1-13 years old)	Not Specified	Normal	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000972 +/- 0.000283 uM	Adult (>18 years old)	Not Specified	Normal	6182788	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.59 uM	Children (1-13 years old)	Female	Odontohypophosphatasia	23093139	details
Blood	Detected and Quantified	0.024 (0.019-0.031) uM	Adult (>18 years old)	Both	Rheumatoid arthritis	16277678	details
Blood	Detected and Quantified	0.251 (0.0310-1.182) uM	Adult (>18 years old)	Both	Hypophosphatasia, infantile	2079838	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.064 uM	Children (1-13 years old)	Not Specified	Truncus arteriosus, seizures and dystonia	21305354	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00243 +/- 0.00138 uM	Adult (>18 years old)	Not Specified	celiac disease	6182788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0119 (0.0036-0.018) uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0036 uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.012 uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.014 uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.018 uM	Newborn (0-30 days old)	Not Specified	PNPO deficiency	18294893	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00500-0.00600 uM	Children (1-13 years old)	Female	Epilepsy, early-onset, vitamin B6-dependent	27912044	details

Associated Disorders and Diseases

Disease References

Rheumatoid arthritis
Chiang EP, Smith DE, Selhub J, Dallal G, Wang YC, Roubenoff R: Inflammation causes tissue-specific depletion of vitamin B6. Arthritis Res Ther. 2005;7(6):R1254-62. Epub 2005 Sep 13. [PubMed:16277678 ]
Hypophosphatasia
Chodirker BN, Coburn SP, Seargeant LE, Whyte MP, Greenberg CR: Increased plasma pyridoxal-5'-phosphate levels before and after pyridoxine loading in carriers of perinatal/infantile hypophosphatasia. J Inherit Metab Dis. 1990;13(6):891-6. [PubMed:2079838 ]
Odontohypophosphatasia
Haliloglu B, Guran T, Atay Z, Abali S, Mornet E, Bereket A, Turan S: Infantile loss of teeth: odontohypophosphatasia or childhood hypophosphatasia. Eur J Pediatr. 2013 Jun;172(6):851-3. doi: 10.1007/s00431-012-1868-4. Epub 2012 Oct 24. [PubMed:23093139 ]
Celiac disease
Hallert C, Allenmark S, Larsson-Cohn U, Sedvall G: High level of pyridoxal 5'-phosphate in the cerebrospinal fluid of adult celiac patients. Am J Clin Nutr. 1982 Nov;36(5):851-4. [PubMed:6182788 ]
Pyridoxamine 5-prime-phosphate oxidase deficiency
Ormazabal A, Oppenheim M, Serrano M, Garcia-Cazorla A, Campistol J, Ribes A, Ruiz A, Moreno J, Hyland K, Clayton P, Heales S, Artuch R: Pyridoxal 5'-phosphate values in cerebrospinal fluid: reference values and diagnosis of PNPO deficiency in paediatric patients. Mol Genet Metab. 2008 Jun;94(2):173-7. doi: 10.1016/j.ymgme.2008.01.004. Epub 2008 Feb 21. [PubMed:18294893 ]
Epilepsy, early-onset, vitamin B6-dependent
Darin N, Reid E, Prunetti L, Samuelsson L, Husain RA, Wilson M, El Yacoubi B, Footitt E, Chong WK, Wilson LC, Prunty H, Pope S, Heales S, Lascelles K, Champion M, Wassmer E, Veggiotti P, de Crecy-Lagard V, Mills PB, Clayton PT: Mutations in PROSC Disrupt Cellular Pyridoxal Phosphate Homeostasis and Cause Vitamin-B6-Dependent Epilepsy. Am J Hum Genet. 2016 Dec 1;99(6):1325-1337. doi: 10.1016/j.ajhg.2016.10.011. [PubMed:27912044 ]

Associated OMIM IDs

180300 (Rheumatoid arthritis)
241500 (Hypophosphatasia)
146300 (Odontohypophosphatasia)
212750 (Celiac disease)
610090 (Pyridoxamine 5-prime-phosphate oxidase deficiency)
617290 (Epilepsy, early-onset, vitamin B6-dependent)

External Links

DrugBank ID

DB00114

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

18405

Food Biomarker Ontology

Not Available

VMH ID

PYDX5P

MarkerDB ID

MDB00000331

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Huang YC, Lan PH, Cheng CH, Lee BJ, Kan MN: Vitamin B6 intakes and status of mechanically ventilated critically ill patients in Taiwan. Eur J Clin Nutr. 2002 May;56(5):387-92. [PubMed:12001008 ]
Huang YC, Chang HH, Huang SC, Cheng CH, Lee BJ, Cheng SY, Su KH: Plasma pyridoxal 5'-phosphate is a significant indicator of immune responses in the mechanically ventilated critically ill. Nutrition. 2005 Jul-Aug;21(7-8):779-85. [PubMed:15975484 ]
Huang YC, Chang SJ, Chiu YT, Chang HH, Cheng CH: The status of plasma homocysteine and related B-vitamins in healthy young vegetarians and nonvegetarians. Eur J Nutr. 2003 Apr;42(2):84-90. [PubMed:12638029 ]
Chiang EP, Selhub J, Bagley PJ, Dallal G, Roubenoff R: Pyridoxine supplementation corrects vitamin B6 deficiency but does not improve inflammation in patients with rheumatoid arthritis. Arthritis Res Ther. 2005;7(6):R1404-11. Epub 2005 Oct 14. [PubMed:16277693 ]
Chiang EP, Bagley PJ, Roubenoff R, Nadeau M, Selhub J: Plasma pyridoxal 5'-phosphate concentration is correlated with functional vitamin B-6 indices in patients with rheumatoid arthritis and marginal vitamin B-6 status. J Nutr. 2003 Apr;133(4):1056-9. [PubMed:12672918 ]
Heiskanen K, Kallio M, Salmenpera L, Siimes MA, Ruokonen I, Perheentupa J: Vitamin B-6 status during childhood: tracking from 2 months to 11 years of age. J Nutr. 1995 Dec;125(12):2985-92. [PubMed:7500176 ]
Longhi RC, Fleisher LD, Tallan HH, Gaull GE: Cystathionine beta-synthase deficiency: a qualitative abnormality of the deficient enzyme modified by vitamin B6 therapy. Pediatr Res. 1977 Feb;11(2):100-3. [PubMed:840498 ]
Fonda ML: Vitamin B6 metabolism and binding to proteins in the blood of alcoholic and nonalcoholic men. Alcohol Clin Exp Res. 1993 Dec;17(6):1171-8. [PubMed:8116826 ]
Lee BJ, Huang MC, Chung LJ, Cheng CH, Lin KL, Su KH, Huang YC: Folic acid and vitamin B12 are more effective than vitamin B6 in lowering fasting plasma homocysteine concentration in patients with coronary artery disease. Eur J Clin Nutr. 2004 Mar;58(3):481-7. [PubMed:14985687 ]
Schuster K, Bailey LB, Cerda JJ, Gregory JF 3rd: Urinary 4-pyridoxic acid excretion in 24-hour versus random urine samples as a measurement of vitamin B6 status in humans. Am J Clin Nutr. 1984 Mar;39(3):466-70. [PubMed:6695847 ]
Heiskanen K, Siimes MA, Perheentupa J, Salmenpera L: Reference ranges for erythrocyte pyridoxal 5'-phosphate concentration and the erythrocyte aspartate transaminase stimulation test in lactating mothers and their infants. Am J Clin Nutr. 1994 Jun;59(6):1297-303. [PubMed:8198054 ]
Selvaag E, Bohmer T, Benkestock K: Reduced serum concentrations of riboflavine and ascorbic acid, and blood thiamine pyrophosphate and pyridoxal-5-phosphate in geriatric patients with and without pressure sores. J Nutr Health Aging. 2002;6(1):75-7. [PubMed:11813090 ]
Iqbal SJ, Plaha DS, Linforth GH, Dalgleish R: Hypophosphatasia: diagnostic application of linked DNA markers in the dominantly inherited adult form. Clin Sci (Lond). 1999 Jul;97(1):73-8. [PubMed:10369796 ]
Heiskanen K, Siimes MA, Salmenpera L, Perheentupa J: Low vitamin B6 status associated with slow growth in healthy breast-fed infants. Pediatr Res. 1995 Nov;38(5):740-6. [PubMed:8552443 ]
Chiang EP, Bagley PJ, Selhub J, Nadeau M, Roubenoff R: Abnormal vitamin B(6) status is associated with severity of symptoms in patients with rheumatoid arthritis. Am J Med. 2003 Mar;114(4):283-7. [PubMed:12681455 ]
Lacour B, Parry C, Drueke T, Touam M, Kreis H, Bailly M, Durand D: Pyridoxal 5'-phosphate deficiency in uremic undialyzed, hemodialyzed, and non-uremic kidney transplant patients. Clin Chim Acta. 1983 Jan 24;127(2):205-15. [PubMed:6337752 ]
Seki T: Combination treatment of high-dose pyridoxal phosphate and low-dose ACTH in children with West syndrome and related disorders. Jpn J Psychiatry Neurol. 1990 Jun;44(2):219-37. [PubMed:1701836 ]
Akopov MA, Kagan ZS, Berezov TT, Filiptsev PIa: [Kinetics and thermodynamics of heat inactivation of L-threonine-L-serine dehydratase from human liver]. Biokhimiia. 1978 Nov;43(11):2027-32. [PubMed:737218 ]
Descombes E, Hanck AB, Fellay G: Water soluble vitamins in chronic hemodialysis patients and need for supplementation. Kidney Int. 1993 Jun;43(6):1319-28. [PubMed:8315945 ]
Stolzenberg-Solomon RZ, Albanes D, Nieto FJ, Hartman TJ, Tangrea JA, Rautalahti M, Sehlub J, Virtamo J, Taylor PR: Pancreatic cancer risk and nutrition-related methyl-group availability indicators in male smokers. J Natl Cancer Inst. 1999 Mar 17;91(6):535-41. [PubMed:10088624 ]

Only showing the first 10 proteins. There are 87 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5-aminolevulinate synthase, erythroid-specific, mitochondrial

General function:: Involved in 5-aminolevulinate synthase activity
Specific function:: Not Available
Gene Name:: ALAS2
Uniprot ID:: P22557
Molecular weight:: 64632.86

Enzyme Details

2. 5-aminolevulinate synthase, nonspecific, mitochondrial

General function:: Involved in 5-aminolevulinate synthase activity
Specific function:: Not Available
Gene Name:: ALAS1
Uniprot ID:: P13196
Molecular weight:: 70580.325

Enzyme Details

3. 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial

General function:: Involved in glycine C-acetyltransferase activity
Specific function:: Not Available
Gene Name:: GCAT
Uniprot ID:: O75600
Molecular weight:: 47973.79

Enzyme Details

4. 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

Enzyme Details

5. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Involved in 4-aminobutyrate transaminase activity
Specific function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:: ABAT
Uniprot ID:: P80404
Molecular weight:: 56438.405

Enzyme Details

6. Tyrosine aminotransferase

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:: TAT
Uniprot ID:: P17735
Molecular weight:: 50398.895

Enzyme Details

7. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Enzyme Details

8. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Enzyme Details

9. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Enzyme Details

10. Branched-chain-amino-acid aminotransferase, cytosolic

General function:: Involved in catalytic activity
Specific function:: Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:: BCAT1
Uniprot ID:: P54687
Molecular weight:: 38644.77

Only showing the first 10 proteins. There are 87 proteins in total.

Show all enzymes and transporters

Showing metabocard for Pyridoxal 5'-phosphate (HMDB0001491)

MOL for HMDB0001491 (Pyridoxal 5'-phosphate)

3D MOL for HMDB0001491 (Pyridoxal 5'-phosphate)

3D SDF for HMDB0001491 (Pyridoxal 5'-phosphate)

3D-SDF for HMDB0001491 (Pyridoxal 5'-phosphate)

PDB for HMDB0001491 (Pyridoxal 5'-phosphate)

3D PDB for HMDB0001491 (Pyridoxal 5'-phosphate)

SMILES for HMDB0001491 (Pyridoxal 5'-phosphate)

INCHI for HMDB0001491 (Pyridoxal 5'-phosphate)

Structure for HMDB0001491 (Pyridoxal 5'-phosphate)

3D Structure for HMDB0001491 (Pyridoxal 5'-phosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes