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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 02:41:23 UTC
Update Date2019-11-12 17:21:36 UTC
HMDB IDHMDB0128416
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-(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
Description5-(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 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. 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-(acetyloxy)-3,14-dihydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5-(acetyloxy)-14-hydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11,13,15-heptaen-13-yl acetate. It is generated by cyp1a2, cyp2b6, cyp2c8, cyp2c9, and cyp2c19 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern3 reaction. This aromatic-hydroxylation-of-fused-benzene-ring-pattern3 occurs in humans.
Structure
Data?1563875384
Synonyms
ValueSource
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 acetic acidGenerator
Chemical FormulaC19H12O9
Average Molecular Weight384.296
Monoisotopic Molecular Weight384.048131966
IUPAC Name5-(acetyloxy)-3,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate
Traditional Name5-(acetyloxy)-3,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=CC(O)=C2C3=C(C4=CC(OC(C)=O)=C(O)C=C4O3)C(=O)OC2=C1
InChI Identifier
InChI=1S/C19H12O9/c1-7(20)25-9-3-12(23)17-15(4-9)28-19(24)16-10-5-14(26-8(2)21)11(22)6-13(10)27-18(16)17/h3-6,22-23H,1-2H3
InChI KeyTUWMMBSXGBQWTM-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
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP3.15ALOGPS
logP2.26ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.19ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area132.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.88 m³·mol⁻¹ChemAxon
Polarizability37.38 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 (2 TMS) - 70eV, Positivesplash10-00dl-2000900000-3f8c62859ca3fa0ca846Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3139000000-3f7b8d345feafc149c2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-0009000000-2c383e88c6c58eda99aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0019000000-ba8409144c1a2516f34bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1094000000-97395986095592b8b92eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0009000000-b682239fb4018218f042Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-3029000000-2cf30ea8739c1b2a8c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-6090000000-1e18d806e0eb2d2efc67Spectrum
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 Compound131834756
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
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 → 3,5,14-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetatedetails