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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 16:07:36 UTC
Update Date2019-11-12 17:22:01 UTC
HMDB IDHMDB0129486
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-{4-[2,3-dioxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]-2,3-dihydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Description6-{4-[2,3-dioxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]-2,3-dihydroxyphenoxy}-3,4,5-trihydroxyoxane-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. 6-{4-[2,3-dioxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]-2,3-dihydroxyphenoxy}-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. 6-{4--2,3-dihydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 1-(2,3,4,6-tetrahydroxyphenyl)-3-(2,3,4-trihydroxyphenyl)propane-1,2-dione. This aromatic-OH-glucuronidation occurs in humans.
Structure
Data?1563875522
Synonyms
ValueSource
6-{4-[2,3-dioxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]-2,3-dihydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC21H20O15
Average Molecular Weight512.376
Monoisotopic Molecular Weight512.080219944
IUPAC Name6-{4-[2,3-dioxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]-2,3-dihydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-{4-[2,3-dioxo-3-(2,3,4,6-tetrahydroxyphenyl)propyl]-2,3-dihydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC1C(O)C(OC2=C(O)C(O)=C(CC(=O)C(=O)C3=C(O)C(O)=C(O)C=C3O)C=C2)OC(C1O)C(O)=O
InChI Identifier
InChI=1S/C21H20O15/c22-6-4-8(24)13(27)15(29)10(6)12(26)7(23)3-5-1-2-9(14(28)11(5)25)35-21-18(32)16(30)17(31)19(36-21)20(33)34/h1-2,4,16-19,21-22,24-25,27-32H,3H2,(H,33,34)
InChI KeyGFMOLUVDKQKNMS-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
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • Butyrophenone
  • Acylphloroglucinol derivative
  • O-glycosyl compound
  • Benzenetriol
  • Phenoxy compound
  • Catechol
  • Aryl ketone
  • Phenol ether
  • Benzoyl
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Alpha-diketone
  • Hydroxy acid
  • Pyran
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • 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
logP1.13ALOGPS
logP0.88ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area271.97 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.41 m³·mol⁻¹ChemAxon
Polarizability44.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014l-4920214000-d823bfcbfb78453282e3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9803400000-aa4899402c05167d5c75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029j-0509630000-47e4d71d01699c1d126cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0914100000-8499eed4a57562c92f50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0911000000-535fd25b57915bf27a39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-2904540000-369d0f8f1b493ef43f6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0903100000-7cad6227738397bef7a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-2913000000-7dfcf3e413166283fd3eSpectrum
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 Compound131835733
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.