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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 03:15:13 UTC
Update Date2019-11-12 17:21:37 UTC
HMDB IDHMDB0128444
Secondary Accession NumbersNone
Metabolite Identification
Common Name6,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl acetate
Description6,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(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. 6,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(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. It is generated by Liver carboxylesterase 1 (P23141) enzyme via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction. 6,13,14-trihydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl acetate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5-(acetyloxy)-6,14-dihydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11,13,15-heptaen-13-yl acetate.
Structure
Data?1563875388
Synonyms
ValueSource
6,13,14-Trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl acetic acidGenerator
Chemical FormulaC17H10O8
Average Molecular Weight342.259
Monoisotopic Molecular Weight342.037567282
IUPAC Name6,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl acetate
Traditional Name6,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C(O)=C3)C(=O)O2
InChI Identifier
InChI=1S/C17H10O8/c1-6(18)23-11-3-2-7-15-13(17(22)25-16(7)14(11)21)8-4-9(19)10(20)5-12(8)24-15/h2-5,19-21H,1H3
InChI KeyMSIHMQGKMSNCAU-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
logP2.62ALOGPS
logP2.35ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.14ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area126.43 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.73 m³·mol⁻¹ChemAxon
Polarizability32.6 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-3100590000-119ba132b908354a6ed7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-5977000000-22d964f6aea00f90694aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0029000000-6720b138c663f3155250Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff3-0079000000-f9001f1508b70233823eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-1190000000-6d1bd8c0bf3b2ee5940bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3059000000-4aae0b995d987e84f83fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052e-4094000000-739207f24d45fed6ed8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8490000000-18c82b2290c10794d9d4Spectrum
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 Compound131834782
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)-6,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-13-yl acetate → 6,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl acetatedetails
6,13,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl acetate → 5,6,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-onedetails