ContaminantDB: Pyridoxal 5'-phosphate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (67)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:04 UTC

Update Date

2026-04-13 20:28:30 UTC

Accession Number

CHEM003367

Identification

Common Name

Pyridoxal 5'-phosphate

Class

Small Molecule

Description

This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Animal Toxin
Dietary Supplement
Drug
Ester
Food Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement
Vitamin B Complex

Chemical Structure

MOL SDF PDB SMILES InChI

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 Mass

247.142 g/mol

Monoisotopic Mass

247.025 g/mol

CAS Registry Number

54-47-7

IUPAC Name

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

Traditional Name

pyridoxal phosphate

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Membrane
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

Erythrocyte
Kidney
Liver
Muscle
Neuron

Pathways

Name	SMPDB Link	KEGG Link
Glucose-Alanine Cycle	SMP00127	Not Available
Malate-Aspartate Shuttle	SMP00129	Not Available
Vitamin B6 Metabolism	SMP00017	map00750
Hypophosphatasia	SMP00503	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	255°C
Boiling Point	Not Available
Solubility	Appreciable

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-0gb9-2690000000-c9bacb7e657461e28407	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-2690000000-c9bacb7e657461e28407	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004j-0910000000-0408f3957221fc9882cd	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gb9-1790000000-b01115fa8b4cfd3612c7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9520000000-bfd574b2e5355694902a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006t-9152000000-26c9f631195663322986	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0f6t-0690000000-4aa57f3f28f0bdef9dcf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0fxx-8900000000-ee972556340c61650528	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9100000000-3cc29fb51820adecd59c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0090000000-9b86e80a9dd0de14ab59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03dj-9800000000-9313aa9cbf19bc6311c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-9500000000-7ce120a58879e2214ce5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004j-9200000000-7e6bd8c298613e59fb5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-4c05178b1645bf01f3fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-3920000000-6c5e6106f5658d1d6c50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-3920000000-f96097815e6922356131	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9000000000-2c4e243699a95e3a0f88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9000000000-8aa111485891af9f0d02	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0090000000-9b86e80a9dd0de14ab59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03dj-9800000000-9313aa9cbf19bc6311c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9500000000-7ce120a58879e2214ce5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-9200000000-7e6bd8c298613e59fb5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-4c05178b1645bf01f3fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002b-9000000000-2c4e243699a95e3a0f88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002b-9000000000-8aa111485891af9f0d02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6t-1790000000-1dcb07cd1110c71f7005	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-ca6aab7f31a36863a417	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9800000000-053802b9c0533d7943ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9080000000-12ca63d34d39d59f6b42	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-144099ec201adbbc4684	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-70a9559d65e78c488e7e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Pyridoxal Phosphate is a coenzyme of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. Pyridoxal phosphate acts as a coenzyme in all transamination reactions, and in some decarboxylation and deamination reactions of amino acids. The aldehyde group of pyridoxal phosphate forms a Schiff-base linkage with the epsilon-amino group of a specific lysine group of the aminotransferase enzyme. The alpha-amino group of the amino acid substrate displaces the epsilon-amino group of the active-site lysine residue. The resulting aldimine becomes deprotonated to become a quinoid intermediate, which in turn accepts a proton at a different position to become a ketimine. The resulting ketimine is hydrolysed so that the amino group remains on the protein complex.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For nutritional supplementation and for treating dietary shortage or imbalance.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00114

HMDB ID

HMDB0001491

FooDB ID

FDB021820

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Robert C. Siegel, “Synthesis of cross-links in the helical domain of collagen using pyridoxal 5-phosphate and copper or iron.” U.S. Patent US4544638, issued June, 1981.

MSDS

Link

General References

1. Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.