Showing Compound Pyridoxal 5'-phosphate (FDB021820)

Record Information

Version

1.0

Creation date

2011-04-11 17:01:47 UTC

Update date

2024-11-29 22:27:57 UTC

Primary ID

FDB021820

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pyridoxal 5'-phosphate

Description

Pyridoxal 5'-phosphate, also known as PLP or codecarboxylase, 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 is a strong basic compound (based on its pKa). 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 milk (cow). 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. This could make pyridoxal 5'-phosphate a potential biomarker for the consumption of these foods. The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal. Pyridoxal 5'-phosphate is a potentially toxic compound. 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.

CAS Number

54-47-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3-Hydroxy-2-methyl-5-[(onooxy)methyl]-4-pyridinecarboxaldehyde	ChEBI
3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-ate	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-ic acid	Generator
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid	Generator
Apolon b6	HMDB
Biosechs	HMDB
Codecarboxylase	ChEBI
Coenzyme b6	HMDB

Showing 1 to 10 of 67 entries

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

Chemical Formula

C8H10NO6P

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

247.1419

Monoisotopic Molecular Weight

247.024573569

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Tissue and substructures:

Muscle

Cell and elements:

Cell:

Nerve cell

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Rheumatoid arthritis

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Pyridoxal 5'-phosphate, 1 MEOX; 3 TMS, GC-MS Spectrum	splash10-0gb9-2690000000-c9bacb7e657461e28407	Spectrum
GC-MS	Pyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrum	splash10-0gb9-2690000000-c9bacb7e657461e28407	Spectrum
GC-MS	Pyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrum	splash10-004j-0910000000-0408f3957221fc9882cd	Spectrum
GC-MS	Pyridoxal 5'-phosphate, non-derivatized, GC-MS Spectrum	splash10-0gb9-1790000000-b01115fa8b4cfd3612c7	Spectrum
Predicted GC-MS	Pyridoxal 5'-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9520000000-bfd574b2e5355694902a	Spectrum
Predicted GC-MS	Pyridoxal 5'-phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006t-9152000000-26c9f631195663322986	Spectrum
Predicted GC-MS	Pyridoxal 5'-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB00114

HMDB ID

HMDB01491

CRC / DFC (Dictionary of Food Compounds) ID

HDV11-W:HDV11-W

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

33526

KNApSAcK ID

Not Available

HET ID

PLP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial	GCAT	O75600
4-aminobutyrate aminotransferase, mitochondrial	ABAT	P80404
5-phosphohydroxy-L-lysine phospho-lyase	AGXT2L2	Q8IUZ5
Alanine aminotransferase 1	GPT	P24298
Alanine aminotransferase 2	GPT2	Q8TD30
Alanine--glyoxylate aminotransferase 2, mitochondrial	AGXT2	Q9BYV1
Aminolevulinate, delta-, synthase 1, isoform CRA_a	ALAS1	Q5JAM2
Aminolevulinate, delta-, synthase 2	ALAS2	Q5JZF5
Arginine decarboxylase	ADC	Q96A70
Aromatic-L-amino-acid decarboxylase	DDC	P20711

Showing 1 to 10 of 57 entries

Pathways

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Name	SMPDB Link	KEGG Link
Glucose-Alanine Cycle	SMP00127	Not Available
Malate-Aspartate Shuttle	SMP00129	Not Available
Metabolism and Physiological Effects of 4-Hydroxyphenylacetic acid	SMP0126879	Not Available
Metabolism and Physiological Effects of Kynurenic Acid	SMP0123300	Not Available
Metabolism and Physiological Effects of N-alpha-Acetyl-L-arginine	SMP0125530	Not Available
Metabolism and Physiological Effects of Oxalic acid	SMP0124875	Not Available
Metabolism and Physiological Effects of p-Cresol sulphate	SMP0126850	Not Available
Metabolism and Physiological Effects of Para-cresol	SMP0123214	Not Available
Metabolism and Physiological Effects of Phenylacetic Acid	SMP0123256	Not Available
Metabolsim and Physiological Effects of 4-Ethylphenylsulfate	SMP0125541	Not Available