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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 02:30:38 UTC
Update Date2019-11-12 17:21:36 UTC
HMDB IDHMDB0128406
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,14-bis(acetyloxy)-6-hydroxy-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
Description5,14-bis(acetyloxy)-6-hydroxy-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 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. 5,14-bis(acetyloxy)-6-hydroxy-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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 5,14-bis(acetyloxy)-6-hydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11,13,15-heptaen-13-yl acetate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5,14-bis(acetyloxy)-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11,13,15-heptaen-13-yl acetate. This aromatic-hydroxylation-of-fused-benzene-ring-pattern2 occurs in humans. It is generated by cyp1a2, cyp2c8, cyp2c9, and cyp3a4 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern2 reaction.
Structure
Data?1563875383
Synonyms
ValueSource
5,14-Bis(acetyloxy)-6-hydroxy-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 acetic acidGenerator
Chemical FormulaC21H14O10
Average Molecular Weight426.333
Monoisotopic Molecular Weight426.058696651
IUPAC Name5,14-bis(acetyloxy)-6-hydroxy-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-13-yl acetate
Traditional Name5,14-bis(acetyloxy)-6-hydroxy-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-13-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=C(O)C2=C(C=C1)C1=C(C3=CC(OC(C)=O)=C(OC(C)=O)C=C3O1)C(=O)O2
InChI Identifier
InChI=1S/C21H14O10/c1-8(22)27-13-5-4-11-19-17(21(26)31-20(11)18(13)25)12-6-15(28-9(2)23)16(29-10(3)24)7-14(12)30-19/h4-7,25H,1-3H3
InChI KeyXHHCREASZQVJGV-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
  • Tricarboxylic acid or derivatives
  • Benzofuran
  • Furopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • 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
logP3.16ALOGPS
logP2.17ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.65ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area138.57 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.04 m³·mol⁻¹ChemAxon
Polarizability41.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01ox-2000900000-f3865cb67a9632d88573Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1109000000-56a6de3c1ca6061cfe7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00p0-0009300000-f944c6984544f140d1a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0173-0009000000-bdf19f9ac622b819868eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0009000000-00a66f57248e7e0191a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-0009400000-2290a70e9eed5cc045e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009100000-0714c6aaa1d0e82f361cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-2019000000-37ae6778bf0d20aac9e1Spectrum
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 Compound131834746
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.