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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:36:21 UTC
Update Date2022-03-07 02:53:52 UTC
HMDB IDHMDB0033831
Secondary Accession Numbers
  • HMDB33831
Metabolite Identification
Common NameMedicagol
DescriptionMedicagol 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. Thus, medicagol is considered to be a flavonoid. Medicagol has been detected, but not quantified in, several different foods, such as breakfast cereal, green tea, pulses, black tea, and teas (Camellia sinensis). This could make medicagol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Medicagol.
Structure
Data?1563862467
Synonyms
ValueSource
3-Hydroxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]-benzopyran-6-one, 9ciHMDB
3-Hydroxy-8,9-methylenedioxycoumestanHMDB
7-Hydroxy-11,12-methylenedioxycoumestanHMDB
7-Hydroxy-5',6'-methylenedioxybenzofurano[3',2':3,4]coumarinHMDB
Chemical FormulaC16H8O6
Average Molecular Weight296.2311
Monoisotopic Molecular Weight296.032087988
IUPAC Name16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaen-20-one
Traditional Namemedicagol
CAS Registry Number1983-72-8
SMILES
OC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2
InChI Identifier
InChI=1S/C16H8O6/c17-7-1-2-8-10(3-7)22-16(18)14-9-4-12-13(20-6-19-12)5-11(9)21-15(8)14/h1-5,17H,6H2
InChI KeyURMVEUAWRUQHON-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
  • Benzodioxole
  • Benzofuran
  • Furopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point324 - 325 °CNot Available
Boiling Point552.00 to 553.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility59.59 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.706 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP2.45ALOGPS
logP2.32ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity73.41 m³·mol⁻¹ChemAxon
Polarizability29.02 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.54431661259
DarkChem[M-H]-167.88731661259
DeepCCS[M+H]+169.66330932474
DeepCCS[M-H]-167.30530932474
DeepCCS[M-2H]-200.78730932474
DeepCCS[M+Na]+176.01430932474
AllCCS[M+H]+166.332859911
AllCCS[M+H-H2O]+162.632859911
AllCCS[M+NH4]+169.832859911
AllCCS[M+Na]+170.832859911
AllCCS[M-H]-168.732859911
AllCCS[M+Na-2H]-167.432859911
AllCCS[M+HCOO]-166.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MedicagolOC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O24323.2Standard polar33892256
MedicagolOC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O22936.2Standard non polar33892256
MedicagolOC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O23115.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Medicagol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC3=C(C=C21)OCO33159.5Semi standard non polar33892256
Medicagol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC3=C(C=C21)OCO33362.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Medicagol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0090000000-a27156413a82b2896b342017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Medicagol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5239000000-a9c7b2d5e4247055cf192017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Medicagol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Medicagol 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 - Medicagol 10V, Positive-QTOFsplash10-0002-0090000000-9e260f2a78964c96d2482016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 20V, Positive-QTOFsplash10-0002-0090000000-f3ea38dbbb02ebbaa19d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 40V, Positive-QTOFsplash10-0uxr-0090000000-66fc3c899f2a8ff81a722016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 10V, Negative-QTOFsplash10-0002-0090000000-07cbe8cbbe681a4d18ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 20V, Negative-QTOFsplash10-0002-0090000000-12c8d5ab4a4d80ea56772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 40V, Negative-QTOFsplash10-0002-1090000000-b9e2a75b068f0418b3272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 10V, Negative-QTOFsplash10-0002-0090000000-f8e22b439b39dc3953892021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 20V, Negative-QTOFsplash10-0002-0090000000-f8e22b439b39dc3953892021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 40V, Negative-QTOFsplash10-00kb-0090000000-583929b0bf872bdc92fc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 10V, Positive-QTOFsplash10-0002-0090000000-8ea6aa97400e7e22a9232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 20V, Positive-QTOFsplash10-0002-0090000000-8ea6aa97400e7e22a9232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Medicagol 40V, Positive-QTOFsplash10-0002-0090000000-15c5acd3c3d21df7c4342021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB011998
KNApSAcK IDC00009760
Chemspider ID4477641
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319322
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1398761
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.. .