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Showing metabocard for 4-Pyridoxolactone (HMDB0003454)

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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 21:21:04 UTC
Update Date2020-02-26 21:24:38 UTC
HMDB IDHMDB0003454
Secondary Accession Numbers
  • HMDB03454
Metabolite Identification
Common Name4-Pyridoxolactone
Description4-Pyridoxolactone, also known as beta-pyracin, 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-Pyridoxolactone is a strong basic compound (based on its pKa). 4-Pyridoxolactone is a bacterial oxidation metabolite of vitamin B6 (KEGG). 4-Pyridoxolactone exists in all eukaryotes, ranging from yeast to humans.
Structure
Data?1582752278
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-Pyridoxic acid lactoneChEBI
4-Pyridoxate lactoneGenerator
beta-PyracinHMDB
Chemical FormulaC8H7NO3
Average Molecular Weight165.1461
Monoisotopic Molecular Weight165.042593095
IUPAC Name7-hydroxy-6-methyl-1H,3H-furo[3,4-c]pyridin-1-one
Traditional Name4-pyridoxolactone
CAS Registry Number4753-19-9
SMILES
CC1=NC=C2COC(=O)C2=C1O
InChI Identifier
InChI=1S/C8H7NO3/c1-4-7(10)6-5(2-9-4)3-12-8(6)11/h2,10H,3H2,1H3
InChI KeyHHPDVQLBYQFYFA-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
  • Methylpyridine
  • Hydroxypyridine
  • Vinylogous acid
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP0.44ALOGPS
logP0.79ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.3ChemAxon
pKa (Strongest Basic)4.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.42 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.05 m³·mol⁻¹ChemAxon
Polarizability15.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-2900000000-5f6a91d1eeb5eaa49adcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-5950000000-11ff12c2dd36530c4236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-aa1266c816944909b39aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-d0258c632349f5e836e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-7900000000-30cd1dadf39f33995b09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-3fd21d96beb6c70780d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-2b177a3586d7e6d68836Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9800000000-3abeb7516d954dda95b1Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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 IDFDB023177
KNApSAcK IDNot Available
Chemspider ID133287
KEGG Compound IDC00971
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6936
PubChem Compound151228
PDB IDNot Available
ChEBI ID16871
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceKorte, Friedhelm; Bannuscher, Herbert. Heterocyclics in metabolism. V. The production of 4-pyridoxic acid and its lactone from pyridoxal-5-phosphate by liver homogenates. Biochemische Zeitschrift (1958), 329 451-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ubbink JB, Serfontein WJ, Becker PJ, De Villiers LS: Determination of urinary 4-pyridoxic acid levels as 4-pyridoxic acid lactone using high-performance liquid chromatography. Am J Clin Nutr. 1986 Nov;44(5):698-703. [PubMed:3766456 ]