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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-13 11:58:51 UTC
Update Date2019-11-12 17:20:58 UTC
HMDB IDHMDB0127323
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
Description6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by Catechol O-methyltransferase (P21964) enzyme via a catechol-O-methylation-pattern2 reaction. 6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4h-chromen-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-chromen-4-one. This catechol-O-methylation-pattern2 occurs in humans.
Structure
Data?1563875235
SynonymsNot Available
Chemical FormulaC22H20O10
Average Molecular Weight444.392
Monoisotopic Molecular Weight444.105646844
IUPAC Name6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
Traditional Name6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O1)C=C(O)C(C1OC(C)C(=O)C(O)C1O)=C2O
InChI Identifier
InChI=1S/C22H20O10/c1-8-18(26)20(28)21(29)22(31-8)17-12(25)7-15-16(19(17)27)11(24)6-13(32-15)9-3-4-10(23)14(5-9)30-2/h3-8,20-23,25,27-29H,1-2H3
InChI KeyZXKDFTZACWMRCV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Chromone
  • Methoxyphenol
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Cyclic ketone
  • 1,2-diol
  • Ketone
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • 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
logP1.76ALOGPS
logP1.45ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.14ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity110.18 m³·mol⁻¹ChemAxon
Polarizability44.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-3100859000-f1ad063d8268db00ee8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i0-3009000000-e40727c5ee70148877aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-b68060222a7831fb15bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2303900000-9d19a502147c133ba224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08i0-4259200000-6301814f539260a27939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0001900000-ab499b5a96dc71201e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-5029600000-a6929109e18a570fdbcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9146000000-4417e391cf99544b781bSpectrum
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 Compound74977692
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.

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one → {2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-6-yl]-4-hydroxy-6-methyl-5-oxooxan-3-yl}oxidanesulfonic aciddetails
6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one → {2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-6-yl]-3-hydroxy-6-methyl-5-oxooxan-4-yl}oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one → 6-{[6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one → 6-{[6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one → 6-{4-[6-(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)-5,7-dihydroxy-4-oxo-4H-chromen-2-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails