Showing Compound 4-Pyridoxic acid (FDB021874)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:20 UTC

Update date

2015-10-09 22:30:36 UTC

Primary ID

FDB021874

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Pyridoxic acid

Description

4-Pyridoxic acid is the catabolic product of vitamin B6 (also known as pyridoxine, pyridoxal and pyradoxamine) which is excreted in the urine. Urinary levels of 4-pyridoxic acid are lower in females than in males and will be reduced in persons with 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 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 as a cofactor. [HMDB]

CAS Number

82-82-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
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

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

Chemical Formula

C8H9NO4

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

183.1614

Monoisotopic Molecular Weight

183.053157781

Classification

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

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	4-Pyridoxic acid, 3 TMS, GC-MS Spectrum	splash10-0600-1594000000-399002a1b2bc22455c9f	Spectrum
GC-MS	4-Pyridoxic acid, non-derivatized, GC-MS Spectrum	splash10-0600-1594000000-399002a1b2bc22455c9f	Spectrum
GC-MS	4-Pyridoxic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0963000000-5ea1f1ffe15dc2478b63	Spectrum
Predicted GC-MS	4-Pyridoxic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uxr-0900000000-fa35397acddd7c3351b8	Spectrum
Predicted GC-MS	4-Pyridoxic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00c0-6029000000-e59f960993866934b8cc	Spectrum
Predicted GC-MS	4-Pyridoxic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Pyridoxic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-4f9434fb63b0ad0ce994	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-0900000000-99753fc7dd56422dd423	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0002-0900000000-6e2e1f60d8bebc0b3340	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0002-6900000000-8c038db01c62f9d4e87b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9200000000-a94133cf31fe1f8b7938	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00kb-0900000000-d57234d89d8c011abfb4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00kb-7900000000-a99b8437514399d65aba	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052r-0900000000-725f61f22b0bc1a28b93	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-0900000000-79e29b063e250dd7037b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-052r-0900000000-725f61f22b0bc1a28b93	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-f82707706c2653c46393	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-4f9434fb63b0ad0ce994	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0900000000-2c70b549625fa141234a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-0900000000-2a37bda24c0b0f98132b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-6900000000-d3f955b006cc32330edd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9200000000-8f0fa7a53eb7325318ba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-0900000000-d57234d89d8c011abfb4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-7900000000-a99b8437514399d65aba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0900000000-df0aa00e8733225ac266	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-5860f1285218e1907916	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-0900000000-463662790c3d6c47c8d1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-6900000000-eda84db35c5bfbd25ceb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-0900000000-cdc1e6701650ec6b77f1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-fd70f5eeff9dec054259	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-ff1dc4213c27146d1751	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum