Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2019-11-26 03:05:54 UTC
Primary IDFDB011998
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 lipid molecule. Medicagol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Medicagol has been detected, but not quantified in, several different foods, such as chickpea, pulses, herbs and spices, alfalfa, and cereals and cereal products. This could make medicagol a potential biomarker for the consumption of these foods.
CAS Number1983-72-8
Structure
Thumb
Synonyms
SynonymSource
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
3-Hydroxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]-benzopyran-6-one, 9CIdb_source
Predicted 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
Chemical FormulaC16H8O6
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
InChI IdentifierInChI=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
Isomeric SMILESOC1=CC2=C(C=C1)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2
Average Molecular Weight296.2311
Monoisotopic Molecular Weight296.032087988
Classification
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

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.87%; H 2.72%; O 32.41%DFC
Melting PointMp 324-325° (337°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-0090000000-a27156413a82b2896b34Spectrum
Predicted GC-MSMedicagol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-0090000000-a27156413a82b2896b34Spectrum
Predicted GC-MSMedicagol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-5239000000-a9c7b2d5e4247055cf19Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-9e260f2a78964c96d248Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-f3ea38dbbb02ebbaa19dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-0090000000-66fc3c899f2a8ff81a72Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-07cbe8cbbe681a4d18edSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-12c8d5ab4a4d80ea5677Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1090000000-b9e2a75b068f0418b327Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-8ea6aa97400e7e22a923Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0090000000-15c5acd3c3d21df7c434Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-8ea6aa97400e7e22a923Spectrum
NMR
TypeDescriptionView
ChemSpider ID4477641
ChEMBL IDCHEMBL99941
KEGG Compound IDNot Available
Pubchem Compound ID5319322
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33831
CRC / DFC (Dictionary of Food Compounds) IDHCK71-E:HCK71-E
EAFUS IDNot Available
Dr. Duke IDMEDICAGOL
BIGG IDNot Available
KNApSAcK IDC00009760
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.