ChemFOnt: Showing chemical card for 4-Pyridoxic acid (CFc000000007)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:34:47 UTC

Chemfont ID

CFc000000007

Molecule Identification

Common Name

4-Pyridoxic acid

Definition

4-Pyridoxic acid is a member of the class of compounds known as methylpyridines. More specifically it is a 2-methylpyridine derivative substituted by a hydroxy group at C-3, a carboxy group at C-4, and a hydroxymethyl group at C-5. 4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) and is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced even further in persons with a riboflavin deficiency. 4-Pyridoxic acid is formed by the action of aldehyde oxidase I (an endogenous enzyme) and by microbial enzymes (pyridoxal 4-dehydrogenase), an NAD-dependent aldehyde dehydrogenase. 4-pyridoxic acid can be further broken down by the gut microflora via the enzyme known as 4-pyridoxic acid dehydrogenase. This enzyme catalyzes the four-electron oxidation of 4-pyridoxic acid to 3-hydroxy-2-methylpyridine-4,5-dicarboxylate, using nicotinamide adenine dinucleotide (NAD) as a cofactor.

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 11068702)
Saliva (HMDB: HMDB0000017)
Cerebrospinal Fluid (CSF) (PMID: 27912044)

Organ

Cell

Erythrocyte (HMDB: HMDB0000017)

Excreta

Biofluid or Excreta

Urine (PMID: 12001008)
Feces (PMID: 24628373)

Cellular substructure

Cytoplasm (HMDB: HMDB0000017)
Extracellular (HMDB: HMDB0000017)

Source

Endogenous

Endogenous (HMDB: HMDB0000017)

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)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Vitamin B6 Metabolism (PathBank: SMP0087395)
Vitamin B6 Metabolism (HMDB: HMDB0000017)

Disease pathway

Hypophosphatasia (HMDB: HMDB0000017)
Hypophosphatasia (PathBank: SMP0120568)

Role

Industrial application

Pharmaceutical industry

Biomarker

Vitamin B6 Consumption (MarkerDB: MDB00000008)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.71 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon