Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 16:15:06 UTC
Update Date2020-02-26 21:25:05 UTC
HMDB IDHMDB0004291
Secondary Accession Numbers
  • HMDB04291
Metabolite Identification
Common Name5-Pyridoxolactone
Description5-Pyridoxolactone belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 5-Pyridoxolactone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 5-pyridoxolactone a potential biomarker for the consumption of these foods. 5-Pyridoxolactone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 5-Pyridoxolactone.
Structure
Data?1582752305
Synonyms
ValueSource
5-Pyridoxic acid lactoneChEBI
5-Pyridoxate lactoneGenerator
3-Carboxy-4-(hydroxymethyl)-5-hydroxy-6-methylpyridine lactoneHMDB
5-Pyridoxic acid g-lactoneHMDB
a-PyracinHMDB
alpha-PyracinHMDB
Pyracin-5HMDB
Pyridoxic acid gamma-lactoneHMDB
Chemical FormulaC8H7NO3
Average Molecular Weight165.1461
Monoisotopic Molecular Weight165.042593095
IUPAC Name7-hydroxy-6-methyl-1H,3H-furo[3,4-c]pyridin-3-one
Traditional Name5-pyridoxolactone
CAS Registry Number4543-56-0
SMILES
CC1=NC=C2C(=O)OCC2=C1O
InChI Identifier
InChI=1S/C8H7NO3/c1-4-7(10)6-3-12-8(11)5(6)2-9-4/h2,10H,3H2,1H3
InChI KeyPPAXBSPBIWBREI-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
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.3 g/LALOGPS
logP0.42ALOGPS
logP0.14ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.42 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.05 m³·mol⁻¹ChemAxon
Polarizability15.44 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.38931661259
DarkChem[M-H]-132.45231661259
DeepCCS[M+H]+133.44530932474
DeepCCS[M-H]-130.9730932474
DeepCCS[M-2H]-166.83930932474
DeepCCS[M+Na]+141.8830932474
AllCCS[M+H]+133.632859911
AllCCS[M+H-H2O]+129.032859911
AllCCS[M+NH4]+137.932859911
AllCCS[M+Na]+139.132859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-133.432859911
AllCCS[M+HCOO]-134.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-PyridoxolactoneCC1=NC=C2C(=O)OCC2=C1O2688.4Standard polar33892256
5-PyridoxolactoneCC1=NC=C2C(=O)OCC2=C1O1560.3Standard non polar33892256
5-PyridoxolactoneCC1=NC=C2C(=O)OCC2=C1O1616.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Pyridoxolactone,1TMS,isomer #1CC1=NC=C2C(=O)OCC2=C1O[Si](C)(C)C1702.1Semi standard non polar33892256
5-Pyridoxolactone,1TBDMS,isomer #1CC1=NC=C2C(=O)OCC2=C1O[Si](C)(C)C(C)(C)C1972.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Pyridoxolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-2900000000-598ecb7d10dd682a3dcf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Pyridoxolactone GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-5950000000-70389cc37e4d8334c9962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Pyridoxolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 10V, Positive-QTOFsplash10-014i-0900000000-e31be06b2625c73bd5f62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 20V, Positive-QTOFsplash10-014i-0900000000-29db0c2d299c687f5d922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 40V, Positive-QTOFsplash10-0avi-9700000000-6941df81fe970e0f77ea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 10V, Negative-QTOFsplash10-03di-0900000000-faffc018b3d55503a74d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 20V, Negative-QTOFsplash10-0229-0900000000-2778bff0e86a1b588ad52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 40V, Negative-QTOFsplash10-0a4i-7900000000-2287674489aef91fbc242017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 10V, Negative-QTOFsplash10-03di-0900000000-65490e650f013cfe115e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 20V, Negative-QTOFsplash10-03di-0900000000-ca0deb64ab0e7aa68bd62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 40V, Negative-QTOFsplash10-0avi-9700000000-96f88c4b6ba8616f8e052021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 10V, Positive-QTOFsplash10-014i-0900000000-52879b1c24e4e827f43a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 20V, Positive-QTOFsplash10-014i-0900000000-68f7008d86f323185b082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Pyridoxolactone 40V, Positive-QTOFsplash10-0fic-9400000000-ff6fdae1aa0cc8c395002021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 IDFDB023360
KNApSAcK IDNot Available
Chemspider ID70672
KEGG Compound IDC06052
BioCyc IDCPD-9028
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78300
PDB IDNot Available
ChEBI ID2124
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHuff, Jesse W.; Perlzweig, Wm. A. A product of oxidative metabolism of pyridoxine, 2-methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridine (4-pyridoxic acid). I. Isolation from urine, structure, and synthesis. Journal of Biological Chemistry (1944), 155 345-55.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mahuren JD, Coburn SP: Determination of 5-pyridoxic acid, 5-pyridoxic acid lactone, and other vitamin B6 compounds by cation-exchange high-performance liquid chromatography. Methods Enzymol. 1997;280:22-9. [PubMed:9211301 ]