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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 03:10:45 UTC
Update Date2019-11-12 17:21:36 UTC
HMDB IDHMDB0128440
Secondary Accession NumbersNone
Metabolite Identification
Common Name13,14,15-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl acetate
Description13,14,15-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-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. 4,5,13,14-tetrahydroxy-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 4,5,14-trihydroxy-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one. 13,14,15-trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by cyp1a2, cyp2b6, cyp2c9, and cyp2e1 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern1 reaction. This aromatic-hydroxylation-of-fused-benzene-ring-pattern1 occurs in humans.
Structure
Data?1563875387
Synonyms
ValueSource
13,14,15-Trihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl acetic acidGenerator
Chemical FormulaC15H8O7
Average Molecular Weight300.222
Monoisotopic Molecular Weight300.027002598
IUPAC Name4,5,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
Traditional Name4,5,13,14-tetrahydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(C=C1O)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2
InChI Identifier
InChI=1S/C15H8O7/c16-7-1-5-11(3-9(7)18)21-14-6-2-8(17)10(19)4-12(6)22-15(20)13(5)14/h1-4,16-19H
InChI KeyNIRCADMUJHDVID-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
  • 6,7-dihydroxycoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • 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
logP2.33ALOGPS
logP1.79ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)7.19ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity73.58 m³·mol⁻¹ChemAxon
Polarizability28.4 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 (4 TMS) - 70eV, Positivesplash10-01b9-3140490000-134edc6178425c8b9b13Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0290000000-2cab05c84967fd7b0e08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-9f3283e39a118f5f5611Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0096000000-0321a1eb296947663b1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056s-2590000000-3f6ed128399599790abfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-85dcea26487989001ec6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-51e17ad73971da0f9409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1790000000-baff6fa80162cf1ebb87Spectrum
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 Compound85554972
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.