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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 21:22:38 UTC
Update Date2019-11-12 17:22:11 UTC
HMDB IDHMDB0129979
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Description6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. 6--3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one. 6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction. This aromatic-OH-glucuronidation occurs in humans.
Structure
Data?1563875587
Synonyms
ValueSource
6-[4-(5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC21H20O11
Average Molecular Weight448.38
Monoisotopic Molecular Weight448.100561464
IUPAC Name6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-[4-(5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC1C(O)C(OC2=CC=C(C=C2)C2COC3=CC(O)=CC(O)=C3C2=O)OC(C1O)C(O)=O
InChI Identifier
InChI=1S/C21H20O11/c22-9-5-12(23)14-13(6-9)30-7-11(15(14)24)8-1-3-10(4-2-8)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,11,16-19,21-23,25-27H,7H2,(H,28,29)
InChI KeyBLWUGIVWYRGHSZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavonoid O-glycosides
Direct ParentIsoflavonoid O-glycosides
Alternative Parents
Substituents
  • Isoflavonoid-4p-o-glycoside
  • Isoflavonoid o-glycoside
  • Isoflavanol
  • Isoflavanone
  • Hydroxyisoflavonoid
  • Isoflavan
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Phenoxy compound
  • Aryl alkyl ketone
  • Phenol ether
  • Aryl ketone
  • Beta-hydroxy acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Ether
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.73ALOGPS
logP0.78ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.69 m³·mol⁻¹ChemAxon
Polarizability42.35 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udj-3352349000-dfa8cb9042cf75b627b5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9116300000-ad9bd037c642f6def5a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ea-0190700000-29f16b0af6cb8a72f926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0590100000-0b7ddcae21bd9cc2caafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-0930000000-d1cbd3a00d409071d5deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fdk-1250900000-94c38797e90ef85b8fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1391200000-1b4a8112a53e2f82bffcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-3390000000-e34b0b7bf131354202a7Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131836189
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.