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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 23:14:25 UTC
Update Date2019-11-12 17:22:16 UTC
HMDB IDHMDB0130253
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,4,5-trihydroxy-6-{4-[3-oxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]phenoxy}oxane-2-carboxylic acid
Description3,4,5-trihydroxy-6-{4-[3-oxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]phenoxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 3,4,5-trihydroxy-6-{4-[3-oxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]phenoxy}oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This aromatic-OH-glucuronidation occurs in humans. 3,4,5-trihydroxy-6-{4-phenoxy}oxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(4-hydroxyphenyl)-1-(2,3,4,6-tetrahydroxyphenyl)propan-1-one. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction.
Structure
Data?1563875622
Synonyms
ValueSource
3,4,5-Trihydroxy-6-{4-[3-oxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]phenoxy}oxane-2-carboxylateGenerator
Chemical FormulaC21H22O12
Average Molecular Weight466.395
Monoisotopic Molecular Weight466.111126148
IUPAC Name3,4,5-trihydroxy-6-{4-[3-oxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]phenoxy}oxane-2-carboxylic acid
Traditional Name3,4,5-trihydroxy-6-{4-[3-oxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]phenoxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC1C(O)C(OC2=CC=C(CCC(=O)C3=C(O)C(O)=C(O)C=C3O)C=C2)OC(C1O)C(O)=O
InChI Identifier
InChI=1S/C21H22O12/c22-10(13-11(23)7-12(24)14(25)15(13)26)6-3-8-1-4-9(5-2-8)32-21-18(29)16(27)17(28)19(33-21)20(30)31/h1-2,4-5,7,16-19,21,23-29H,3,6H2,(H,30,31)
InChI KeyRXOUSSLDPXRDIG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • 2'-hydroxy-dihydrochalcone
  • Linear 1,3-diarylpropanoid
  • Cinnamylphenol
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Alkyl-phenylketone
  • Glucuronic acid or derivatives
  • Butyrophenone
  • Acylphloroglucinol derivative
  • O-glycosyl compound
  • Glycosyl compound
  • Phenylketone
  • Benzenetriol
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Phenoxy compound
  • Benzoyl
  • Beta-hydroxy acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Monosaccharide
  • Pyran
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Polyol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP1.1ALOGPS
logP1.64ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area214.44 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.7 m³·mol⁻¹ChemAxon
Polarizability44.66 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aov-9526300000-1d17ebb161a20e49116eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kg-0380900000-bfd049ff2f45e4f477d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r6-0960000000-19c19470eb3ff0b69084Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-0930000000-24456d8da3506b1faa9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-1340900000-866ce9ceca03dae182f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-2970400000-6f3e1a368cb425f01b51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001c-4980000000-34604f80e604e255ddacSpectrum
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
FoodDB 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 Compound131836439
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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.