Bovine Metabolome Database: Showing metabocard for 4-Pyridoxic acid (BMDB0000017)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:18:30 UTC

Update Date

2020-05-21 16:28:54 UTC

BMDB ID

BMDB0000017

Secondary Accession Numbers

BMDB00017

Metabolite Identification

Common Name

4-Pyridoxic acid

Description

4-4-4-pyridoxic acid, also known as 4-4-pyridoxic acid, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 4-4-4-pyridoxic acid exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. 4-4-4-pyridoxic acid exists in all living organisms, ranging from bacteria to humans. 4-4-4-pyridoxic acid can be biosynthesized from pyridoxal; which is catalyzed by the enzyme aldehyde oxidase. In cattle, 4-4-pyridoxic acid is involved in the metabolic pathway called the vitamin B6 metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridine	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylic acid	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinic acid	ChEBI
4-Pyridoxinecarboxylic acid	ChEBI
4-Pyridoxinic acid	ChEBI
4-Pyridoxinsaeure	ChEBI
4-Pyridoxylic acid	ChEBI
Pyridoxic acid	ChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylate	Generator
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinate	Generator
4-Pyridoxinecarboxylate	Generator
4-Pyridoxinate	Generator
4-Pyridoxylate	Generator
Pyridoxate	Generator
4-Pyridoxate	Generator
3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinate	HMDB
3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinic acid	HMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinate	HMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinic acid	HMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinsaeure	HMDB
4 Pyridoxinic acid	MeSH, HMDB
Pyridoxinecarboxylic acid	MeSH, HMDB
4 Pyridoxylic acid	MeSH, HMDB
4 Pyridoxic acid	MeSH, HMDB

Chemical Formula

C₈H₉NO₄

Average Molecular Weight

183.1614

Monoisotopic Molecular Weight

183.053157781

IUPAC Name

3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid

Traditional Name

pyridoxic acid

CAS Registry Number

82-82-6

SMILES

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

InChI Identifier

InChI=1S/C8H9NO4/c1-4-7(11)6(8(12)13)5(3-10)2-9-4/h2,10-11H,3H2,1H3,(H,12,13)

InChI Key

HXACOUQIXZGNBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Hydroxypyridine
Methylpyridine
Vinylogous acid
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monohydroxypyridine (CHEBI:17405 )
methylpyridines (CHEBI:17405 )
vitamin B6 (CHEBI:17405 )
hydroxymethylpyridine (CHEBI:17405 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	247 - 248 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.08	ALOGPS
logP	-0.75	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	4.09	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.55 m³·mol⁻¹	ChemAxon
Polarizability	17.19 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0600-1594000000-399002a1b2bc22455c9f	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0600-1594000000-399002a1b2bc22455c9f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0963000000-5ea1f1ffe15dc2478b63	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-0900000000-fa35397acddd7c3351b8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00c0-6029000000-e59f960993866934b8cc	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-4f9434fb63b0ad0ce994	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-0900000000-99753fc7dd56422dd423	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0002-0900000000-6e2e1f60d8bebc0b3340	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0002-6900000000-8c038db01c62f9d4e87b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9200000000-a94133cf31fe1f8b7938	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00kb-0900000000-d57234d89d8c011abfb4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00kb-7900000000-a99b8437514399d65aba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052r-0900000000-725f61f22b0bc1a28b93	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-0900000000-79e29b063e250dd7037b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-052r-0900000000-725f61f22b0bc1a28b93	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-f82707706c2653c46393	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-4f9434fb63b0ad0ce994	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0900000000-2c70b549625fa141234a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-0900000000-2a37bda24c0b0f98132b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-6900000000-d3f955b006cc32330edd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9200000000-8f0fa7a53eb7325318ba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-0900000000-d57234d89d8c011abfb4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-7900000000-a99b8437514399d65aba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0900000000-df0aa00e8733225ac266	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-5860f1285218e1907916	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-0900000000-463662790c3d6c47c8d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-6900000000-eda84db35c5bfbd25ceb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-0900000000-cdc1e6701650ec6b77f1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-fd70f5eeff9dec054259	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-ff1dc4213c27146d1751	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Bladder
Erythrocyte
Kidney
Liver
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Vitamin B6 Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Erythrocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000017

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

239

PubChem Compound

6723

PDB ID

Not Available

ChEBI ID

17405

References

Synthesis Reference

Senkuma, Masahiko; Imada, Katsumi; Sato, Masatada. Preparation of 4-pyridoxic acid. Jpn. Kokai Tokkyo Koho (1992), 2 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Aldehyde oxidase 1

General function:: Nucleotide transport and metabolism
Specific function:: Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. Also may catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis.
Gene Name:: AOX1
Uniprot ID:: P48034
Molecular weight:: 147611.0

Reactions

Pyridoxal + Oxygen + Water → 4-Pyridoxic acid + Hydrogen peroxide	details

Showing metabocard for 4-Pyridoxic acid (BMDB0000017)

Structure for BMDB0000017 (4-Pyridoxic acid)

Enzymes

Reactions