You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusPredicted
Creation Date2017-09-12 18:33:25 UTC
Update Date2019-11-12 17:20:07 UTC
HMDB IDHMDB0124839
Secondary Accession NumbersNone
Metabolite Identification
Common Name6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one
Description6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 6,12-bis(3,4-dihydroxyphenyl)-13-hydroxy-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-4-one. It is generated by EC.3.2.1.X enzyme via a glycoside-hydrolysis reaction. This glycoside-hydrolysis occurs in humans.
Structure
Data?1563874899
SynonymsNot Available
Chemical FormulaC24H20O9
Average Molecular Weight452.415
Monoisotopic Molecular Weight452.110732224
IUPAC Name6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-4-one
Traditional Name6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-4-one
CAS Registry NumberNot Available
SMILES
OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C=C(O)C1=C2OC(=O)CC1C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C24H20O9/c25-14-3-1-10(5-16(14)27)12-8-21(31)33-24-13-7-19(30)23(11-2-4-15(26)17(28)6-11)32-20(13)9-18(29)22(12)24/h1-6,9,12,19,23,25-30H,7-8H2
InChI KeyAKZBEMDOKOHIFM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • Pyranoflavonoid
  • Linear 1,7-diphenylheptane skeleton
  • Pyranoneoflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Neoflavan
  • Neoflavonoid skeleton
  • Angular pyranocoumarin
  • Pyranocoumarin
  • Pyranochromene
  • 3,4-dihydrocoumarin
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • 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
logP2.32ALOGPS
logP2.83ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.7ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity115.02 m³·mol⁻¹ChemAxon
Polarizability44.67 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-0udi-3010039000-0e052f94b90258f33025Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0401900000-00dd80069486c2f9a396Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0144900000-c2e95ef5c06e3bd39b2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0393600000-abf3a70121fdab61e2f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ei-0960100000-eb3a0a590dfb41477bd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0020900000-ecc717b6ab86c09b0b55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0981700000-643eb5aed18d5b2ae305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2490200000-081d7d803374dec6cb70Spectrum
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 IDFDB083761
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73822599
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
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → 12-(3,4-dihydroxyphenyl)-8,13-dihydroxy-6-(4-hydroxy-3-methoxyphenyl)-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-onedetails
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → 6-(3,4-dihydroxyphenyl)-8,13-dihydroxy-12-(4-hydroxy-3-methoxyphenyl)-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-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
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → [6,12-bis(3,4-dihydroxyphenyl)-8-hydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-13-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
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → 6-{4-[12-(3,4-dihydroxyphenyl)-8,13-dihydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-6-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → 6-{5-[12-(3,4-dihydroxyphenyl)-8,13-dihydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-6-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → 6-{4-[6-(3,4-dihydroxyphenyl)-8,13-dihydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-12-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → 6-{5-[6-(3,4-dihydroxyphenyl)-8,13-dihydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-12-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → 6-{[6,12-bis(3,4-dihydroxyphenyl)-13-hydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-trien-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → {5-[12-(3,4-dihydroxyphenyl)-8,13-dihydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-6-yl]-2-hydroxyphenyl}oxidanesulfonic aciddetails
6,12-bis(3,4-dihydroxyphenyl)-8,13-dihydroxy-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-4-one → {5-[6-(3,4-dihydroxyphenyl)-8,13-dihydroxy-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8-trien-12-yl]-2-hydroxyphenyl}oxidanesulfonic aciddetails