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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:39:22 UTC
Update Date2019-07-23 06:14:35 UTC
HMDB IDHMDB0033883
Secondary Accession Numbers
  • HMDB33883
Metabolite Identification
Common Name3-O-Methylglycyrol
Description3-O-Methylglycyrol 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, 3-O-methylglycyrol is considered to be a flavonoid lipid molecule. 3-O-Methylglycyrol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-O-methylglycyrol has been detected, but not quantified in, root vegetables. This could make 3-O-methylglycyrol a potential biomarker for the consumption of these foods.
Structure
Data?1563862475
Synonyms
ValueSource
5-O-MethylglycryolHMDB
1-O-MethylglycyrolHMDB
5-O-MethylglycyrolHMDB
9-Hydroxy-1,3-dimethoxy-2-prenylcoumestanHMDB
Chemical FormulaC22H20O6
Average Molecular Weight380.3906
Monoisotopic Molecular Weight380.125988372
IUPAC Name14-hydroxy-3,5-dimethoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
Traditional Name14-hydroxy-3,5-dimethoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
CAS Registry Number23013-85-6
SMILES
COC1=CC2=C(C3=C(C4=C(O3)C=C(O)C=C4)C(=O)O2)C(OC)=C1CC=C(C)C
InChI Identifier
InChI=1S/C22H20O6/c1-11(2)5-7-14-15(25-3)10-17-19(20(14)26-4)21-18(22(24)28-17)13-8-6-12(23)9-16(13)27-21/h5-6,8-10,23H,7H2,1-4H3
InChI KeyACDSUMGMZHXCRO-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
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point259 - 260.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP4.03ALOGPS
logP4.11ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.1ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.81 m³·mol⁻¹ChemAxon
Polarizability40.73 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 (Non-derivatized) - 70eV, Positivesplash10-0uxr-1029000000-1131f5ab96fe42ebe6d8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-3042900000-62966d356650e506ad88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-12529f7b58f64e247559Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-2009000000-76be04b414386aa5e490Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9125000000-0c80d04dec186f283667Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-23cd7ebedbe60ac144faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-fb5349b915847901eae3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1469000000-a96778907d3e89c9c1e9Spectrum
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 IDFDB012076
KNApSAcK IDC00009780
Chemspider ID4477913
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319666
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .