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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 02:56:22 UTC
Update Date2019-11-12 17:21:36 UTC
HMDB IDHMDB0128429
Secondary Accession NumbersNone
Metabolite Identification
Common Name13-(acetyloxy)-5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl acetate
Description13-(acetyloxy)-5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-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. 13-(acetyloxy)-5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). 13-(acetyloxy)-5,12-dihydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl acetate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 14-(acetyloxy)-5-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?1563875386
Synonyms
ValueSource
13-(Acetyloxy)-5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl acetic acidGenerator
Chemical FormulaC19H12O9
Average Molecular Weight384.296
Monoisotopic Molecular Weight384.048131966
IUPAC Name13-(acetyloxy)-5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl acetate
Traditional Name13-(acetyloxy)-5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=C(OC(C)=O)C(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1
InChI Identifier
InChI=1S/C19H12O9/c1-7(20)25-13-6-12-14(16(23)18(13)26-8(2)21)15-17(27-12)10-4-3-9(22)5-11(10)28-19(15)24/h3-6,22-23H,1-2H3
InChI KeyKWCRHKUIYUIPDY-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
logP3.1ALOGPS
logP2.26ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area132.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.88 m³·mol⁻¹ChemAxon
Polarizability37.09 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-3000910000-6f99c49aa071be6402ceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3049000000-4a9664636e401dab9d43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-0009000000-68b388238d4934dcb0e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-0019000000-181aa828d73e3185ed6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1093000000-bf75cec74c1684eb2486Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1009000000-a7ab3a10aead05560078Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-3039000000-036f2f684bf3454e2e37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9060000000-39fc040b5184aa8b60fbSpectrum
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 Compound131834769
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.