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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:38 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030560
Secondary Accession Numbers
  • HMDB30560
Metabolite Identification
Common Name7,11,12-Triacetoxycoumestan
Description7,11,12-Triacetoxycoumestan, also known as stimol 410, 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. 7,11,12-Triacetoxycoumestan is an extremely weak basic (essentially neutral) compound (based on its pKa). Animal growth stimulan.
Structure
Data?1563862004
Synonyms
ValueSource
Stimol 410HMDB
5,14-Bis(acetyloxy)-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 FormulaC21H14O9
Average Molecular Weight410.3305
Monoisotopic Molecular Weight410.063782046
IUPAC Name13,14-bis(acetyloxy)-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
Traditional Name13,14-bis(acetyloxy)-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
CAS Registry Number2074-56-8
SMILES
CC(=O)OC1=CC2=C(C=C1)C1=C(C3=CC(OC(C)=O)=C(OC(C)=O)C=C3O1)C(=O)O2
InChI Identifier
InChI=1S/C21H14O9/c1-9(22)26-12-4-5-13-15(6-12)30-21(25)19-14-7-17(27-10(2)23)18(28-11(3)24)8-16(14)29-20(13)19/h4-8H,1-3H3
InChI KeyXZTLRBKHOHDMTG-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point255 - 257 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP3.29ALOGPS
logP1.83ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area118.34 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.05 m³·mol⁻¹ChemAxon
Polarizability40.2 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.24431661259
DarkChem[M-H]-192.93831661259
DeepCCS[M+H]+189.3230932474
DeepCCS[M-H]-186.96230932474
DeepCCS[M-2H]-220.24330932474
DeepCCS[M+Na]+195.42830932474
AllCCS[M+H]+192.632859911
AllCCS[M+H-H2O]+189.932859911
AllCCS[M+NH4]+195.132859911
AllCCS[M+Na]+195.832859911
AllCCS[M-H]-194.732859911
AllCCS[M+Na-2H]-194.432859911
AllCCS[M+HCOO]-194.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7,11,12-TriacetoxycoumestanCC(=O)OC1=CC2=C(C=C1)C1=C(C3=CC(OC(C)=O)=C(OC(C)=O)C=C3O1)C(=O)O24718.3Standard polar33892256
7,11,12-TriacetoxycoumestanCC(=O)OC1=CC2=C(C=C1)C1=C(C3=CC(OC(C)=O)=C(OC(C)=O)C=C3O1)C(=O)O23519.8Standard non polar33892256
7,11,12-TriacetoxycoumestanCC(=O)OC1=CC2=C(C=C1)C1=C(C3=CC(OC(C)=O)=C(OC(C)=O)C=C3O1)C(=O)O23433.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7,11,12-Triacetoxycoumestan GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-1109000000-352a54812cb4641a6ff02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7,11,12-Triacetoxycoumestan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7,11,12-Triacetoxycoumestan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 10V, Positive-QTOFsplash10-02t9-0009400000-939f828d4465e05236962016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 20V, Positive-QTOFsplash10-016r-0009100000-104aa8661812839342e02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 40V, Positive-QTOFsplash10-004i-1009000000-6af9435345c47497bd302016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 10V, Negative-QTOFsplash10-066r-0009400000-0f93e6f2da4af589531d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 20V, Negative-QTOFsplash10-014i-0009100000-24e3f1d417cfb270cc502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 40V, Negative-QTOFsplash10-00b9-2019000000-d32b43ff9d53dcbc87032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 10V, Negative-QTOFsplash10-016r-0009200000-9a24d9db152d23195d962021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 20V, Negative-QTOFsplash10-0100-0009000000-891c2b8387e41511bb9e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 40V, Negative-QTOFsplash10-0092-0039000000-5e4b7f53ba086f2533082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 10V, Positive-QTOFsplash10-03di-0004900000-14df8e963ba13f8312542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 20V, Positive-QTOFsplash10-02di-0009200000-b10bf2858cc5398254282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7,11,12-Triacetoxycoumestan 40V, Positive-QTOFsplash10-004i-0009000000-18996f57b5bf15545b1a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002444
KNApSAcK IDNot Available
Chemspider ID894000
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1040837
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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
7,11,12-Triacetoxycoumestan → 5-(acetyloxy)-14-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 acetatedetails
7,11,12-Triacetoxycoumestan → Acetic aciddetails
7,11,12-Triacetoxycoumestan → 5-(acetyloxy)-13-hydroxy-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 acetatedetails
7,11,12-Triacetoxycoumestan → 14-(acetyloxy)-5-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 acetatedetails