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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 03:25:02 UTC
Update Date2019-11-12 17:21:37 UTC
HMDB IDHMDB0128452
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetate
Description3,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetate belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. 3,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). This hydrolysis-of-carboxylic-acid-ester-pattern1 occurs in human gut microbiota. 3,13,14-trihydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5-(acetyloxy)-3,14-dihydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate. It is generated by Liver carboxylesterase 1 (P23141) enzyme via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction.
Structure
Data?1563875389
Synonyms
ValueSource
3,13,14-Trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetic acidGenerator
Chemical FormulaC17H10O8
Average Molecular Weight342.259
Monoisotopic Molecular Weight342.037567282
IUPAC Name3,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetate
Traditional Name3,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=CC(O)=C2C3=C(C4=C(O3)C=C(O)C(O)=C4)C(=O)OC2=C1
InChI Identifier
InChI=1S/C17H10O8/c1-6(18)23-7-2-11(21)15-13(3-7)25-17(22)14-8-4-9(19)10(20)5-12(8)24-16(14)15/h2-5,19-21H,1H3
InChI KeyQNUQRVLVWQSKQF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Furanocoumarin
  • Angular furanocoumarin
  • Coumarin
  • 1-benzopyran
  • Benzopyran
  • Benzofuran
  • Furopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP2.7ALOGPS
logP1.7ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.19ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area126.43 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.73 m³·mol⁻¹ChemAxon
Polarizability32.52 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, Positivesplash10-0udl-3100590000-1054ad7c96fd112360f4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-4396000000-a973efafaf464bbb6b1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0019000000-fd2de00de0b191117bf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0097000000-8cb922974ce6410c4625Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-1090000000-3ae4a8dbd13e139e0282Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-1089000000-fec40461618dfec3b421Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052e-3093000000-ab789b4c51c74d5ba333Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3190000000-d1ad9d621e8816f8a3a7Spectrum
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 Compound131834790
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:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
5-(acetyloxy)-3,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate → 3,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetatedetails
3,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl acetate → 3,5,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-onedetails