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Record Information
Version1.0
Creation Date2016-09-30 22:18:30 UTC
Update Date2020-03-18 18:12:00 UTC
BMDB IDBMDB0000017
Secondary Accession Numbers
  • BMDB00017
Metabolite Identification
Common Name4-Pyridoxic acid
Description4-4-4-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
Thumb
Synonyms
ValueSource
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
Chemical FormulaC8H9NO4
Average Molecular Weight183.1614
Monoisotopic Molecular Weight183.053157781
IUPAC Name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid
Traditional Namepyridoxic acid
CAS Registry Number82-82-6
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 KeyHXACOUQIXZGNBF-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.
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
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point247 - 248 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0600-1594000000-399002a1b2bc22455c9fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0600-1594000000-399002a1b2bc22455c9fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0963000000-5ea1f1ffe15dc2478b63View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-0900000000-fa35397acddd7c3351b8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00c0-6029000000-e59f960993866934b8ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-4f9434fb63b0ad0ce994View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-0900000000-99753fc7dd56422dd423View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-0900000000-6e2e1f60d8bebc0b3340View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0002-6900000000-8c038db01c62f9d4e87bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9200000000-a94133cf31fe1f8b7938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-0900000000-d57234d89d8c011abfb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kb-7900000000-a99b8437514399d65abaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0900000000-725f61f22b0bc1a28b93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0900000000-79e29b063e250dd7037bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-0900000000-725f61f22b0bc1a28b93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f82707706c2653c46393View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-4f9434fb63b0ad0ce994View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-2c70b549625fa141234aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-2a37bda24c0b0f98132bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-6900000000-d3f955b006cc32330eddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9200000000-8f0fa7a53eb7325318baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0900000000-d57234d89d8c011abfb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-7900000000-a99b8437514399d65abaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-df0aa00e8733225ac266View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-5860f1285218e1907916View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-0900000000-463662790c3d6c47c8d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-6900000000-eda84db35c5bfbd25cebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-cdc1e6701650ec6b77f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-fd70f5eeff9dec054259View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-ff1dc4213c27146d1751View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Bladder
  • Erythrocyte
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Vitamin B6 MetabolismSMP0087240Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021874
KNApSAcK IDNot Available
Chemspider ID6467
KEGG Compound IDC00847
BioCyc IDCPD-1112
BiGG ID36190
Wikipedia LinkNot Available
METLIN ID239
PubChem Compound6723
PDB IDNot Available
ChEBI ID17405
References
Synthesis ReferenceSenkuma, 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 ReferencesNot Available