Record Information
Version1.0
Creation date2011-09-21 00:04:20 UTC
Update date2015-10-09 22:30:36 UTC
Primary IDFDB021874
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Pyridoxic acid
Description4-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 Number82-82-6
Structure
Thumb
Synonyms
SynonymSource
2-Methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridineChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinic acidChEBI
4-PyridoxateChEBI
4-Pyridoxinecarboxylic acidChEBI
4-Pyridoxinic acidChEBI
4-Pyridoxylic acidChEBI
Pyridoxic acidChEBI
3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinateGenerator
4-PyridoxinecarboxylateGenerator
4-PyridoxinateGenerator
4-PyridoxylateGenerator
PyridoxateGenerator
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylateHMDB
3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylic acidHMDB
3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinateHMDB
3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinic acidHMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinateHMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinic acidHMDB
3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinsaeureHMDB
4-PyridoxinsaeureHMDB
4 Pyridoxinic acidHMDB
Pyridoxinecarboxylic acidHMDB
4 Pyridoxylic acidHMDB
4 Pyridoxic acidHMDB
3-hydroxy-5-(hydroxymethyl)-2-methyl-Isonicotinatehmdb
3-hydroxy-5-(hydroxymethyl)-2-methyl-Isonicotinic acidhmdb
3-hydroxy-5-hydroxymethyl-2-methyl-isonicotinatehmdb
3-hydroxy-5-hydroxymethyl-2-methyl-isonicotinic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility8.71 g/LALOGPS
logP-0.08ALOGPS
logP-0.75ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.55ChemAxon
pKa (Strongest Basic)4.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.55 m³·mol⁻¹ChemAxon
Polarizability17.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H9NO4
IUPAC name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid
InChI IdentifierInChI=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 KeyHXACOUQIXZGNBF-UHFFFAOYSA-N
Isomeric SMILESCC1=NC=C(CO)C(C(O)=O)=C1O
Average Molecular Weight183.1614
Monoisotopic Molecular Weight183.053157781
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS4-Pyridoxic acid, 3 TMS, GC-MS Spectrumsplash10-0600-1594000000-399002a1b2bc22455c9fSpectrum
GC-MS4-Pyridoxic acid, non-derivatized, GC-MS Spectrumsplash10-0600-1594000000-399002a1b2bc22455c9fSpectrum
GC-MS4-Pyridoxic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0963000000-5ea1f1ffe15dc2478b63Spectrum
Predicted GC-MS4-Pyridoxic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uxr-0900000000-fa35397acddd7c3351b8Spectrum
Predicted GC-MS4-Pyridoxic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00c0-6029000000-e59f960993866934b8ccSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-4f9434fb63b0ad0ce994Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-0900000000-99753fc7dd56422dd423Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-0900000000-6e2e1f60d8bebc0b3340Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0002-6900000000-8c038db01c62f9d4e87bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9200000000-a94133cf31fe1f8b7938Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-0900000000-d57234d89d8c011abfb4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kb-7900000000-a99b8437514399d65abaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0900000000-725f61f22b0bc1a28b93Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0900000000-79e29b063e250dd7037bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-0900000000-725f61f22b0bc1a28b93Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f82707706c2653c46393Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-4f9434fb63b0ad0ce994Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-2c70b549625fa141234aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-2a37bda24c0b0f98132bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-6900000000-d3f955b006cc32330eddSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9200000000-8f0fa7a53eb7325318baSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0900000000-d57234d89d8c011abfb4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-7900000000-a99b8437514399d65abaSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-df0aa00e8733225ac266Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-5860f1285218e1907916Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-0900000000-463662790c3d6c47c8d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-eda84db35c5bfbd25cebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-cdc1e6701650ec6b77f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-fd70f5eeff9dec054259Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-ff1dc4213c27146d1751Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID6467
ChEMBL IDNot Available
KEGG Compound IDC00847
Pubchem Compound ID6723
Pubchem Substance IDNot Available
ChEBI ID17405
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00017
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36190
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Vitamin B6 MetabolismSMP00017 map00750
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference