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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 04:33:12 UTC
Update Date2019-11-12 17:21:39 UTC
HMDB IDHMDB0128549
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one
Description5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4h-chromen-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4h-chromen-4-one. It is generated by cyp2b6 enzyme via a hydroxylation-of-benzene-para-to-strongly-edg reaction. This hydroxylation-of-benzene-para-to-strongly-edg occurs in humans.
Structure
Data?1563875401
SynonymsNot Available
Chemical FormulaC22H22O12
Average Molecular Weight478.406
Monoisotopic Molecular Weight478.111126148
IUPAC Name5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one
Traditional Name5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2O)C(O)=C1C1OC(CO)C(O)C(O)C1O
InChI Identifier
InChI=1S/C22H22O12/c1-32-13-5-14-16(11(27)4-12(33-14)7-2-9(25)10(26)3-8(7)24)19(29)17(13)22-21(31)20(30)18(28)15(6-23)34-22/h2-5,15,18,20-26,28-31H,6H2,1H3
InChI KeyZUWSWSWQQOXFSN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid c-glycosides. These 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
  • 7-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Hydroxyquinol derivative
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen 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
logP0.41ALOGPS
logP-0.51ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)6.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity114.48 m³·mol⁻¹ChemAxon
Polarizability46.39 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fh9-3100019000-7ff6837bfa1833fb97e1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00vi-3109600000-3950ad172dda6e001b81JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0001900000-fa8259db52116ec71faaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-2202900000-fb66c3020b2c15816b53JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016u-2369300000-532492a440a4ba7ace58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-05c9d4bb7aa34c2dbf30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adj-4207900000-f17f424b4793f3ce839cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8429500000-2f2742499507d9007107JSpectraViewer
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 CompoundNot Available
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 magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → 2-(2,5-dihydroxy-4-methoxyphenyl)-5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-onedetails
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
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → ({3,4,5-trihydroxy-6-[5-hydroxy-7-methoxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]oxan-2-yl}methoxy)sulfonic aciddetails
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → {4,5-dihydroxy-2-[5-hydroxy-7-methoxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → {3,5-dihydroxy-2-[5-hydroxy-7-methoxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → {4,5-dihydroxy-6-[5-hydroxy-7-methoxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]-2-(hydroxymethyl)oxan-3-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
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → 6-(4,5-dihydroxy-2-{5-hydroxy-7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → 3,4,5-trihydroxy-6-({7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-5-yl}oxy)oxane-2-carboxylic aciddetails
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → 6-(2,5-dihydroxy-4-{5-hydroxy-7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one → 6-(2,4-dihydroxy-5-{5-hydroxy-7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails