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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:39:22 UTC
Update Date2022-03-07 02:53:53 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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point259 - 260.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.06231661259
DarkChem[M-H]-189.47131661259
DeepCCS[M+H]+194.95830932474
DeepCCS[M-H]-192.56230932474
DeepCCS[M-2H]-226.00630932474
DeepCCS[M+Na]+201.04230932474
AllCCS[M+H]+190.832859911
AllCCS[M+H-H2O]+187.832859911
AllCCS[M+NH4]+193.632859911
AllCCS[M+Na]+194.432859911
AllCCS[M-H]-191.432859911
AllCCS[M+Na-2H]-190.932859911
AllCCS[M+HCOO]-190.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-O-MethylglycyrolCOC1=CC2=C(C3=C(C4=C(O3)C=C(O)C=C4)C(=O)O2)C(OC)=C1CC=C(C)C4500.9Standard polar33892256
3-O-MethylglycyrolCOC1=CC2=C(C3=C(C4=C(O3)C=C(O)C=C4)C(=O)O2)C(OC)=C1CC=C(C)C3482.2Standard non polar33892256
3-O-MethylglycyrolCOC1=CC2=C(C3=C(C4=C(O3)C=C(O)C=C4)C(=O)O2)C(OC)=C1CC=C(C)C3584.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-O-Methylglycyrol,1TMS,isomer #1COC1=CC2=C(C(OC)=C1CC=C(C)C)C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C)C=C2O13521.9Semi standard non polar33892256
3-O-Methylglycyrol,1TBDMS,isomer #1COC1=CC2=C(C(OC)=C1CC=C(C)C)C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O13729.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-O-Methylglycyrol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-1029000000-1131f5ab96fe42ebe6d82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-O-Methylglycyrol GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-3042900000-62966d356650e506ad882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-O-Methylglycyrol 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 - 3-O-Methylglycyrol 10V, Positive-QTOFsplash10-001i-0009000000-12529f7b58f64e2475592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 20V, Positive-QTOFsplash10-00lr-2009000000-76be04b414386aa5e4902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 40V, Positive-QTOFsplash10-0gb9-9125000000-0c80d04dec186f2836672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 10V, Negative-QTOFsplash10-004i-0009000000-23cd7ebedbe60ac144fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 20V, Negative-QTOFsplash10-004i-0009000000-fb5349b915847901eae32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 40V, Negative-QTOFsplash10-00lr-1469000000-a96778907d3e89c9c1e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 10V, Positive-QTOFsplash10-001i-0009000000-bc8cb05283f86856cae42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 20V, Positive-QTOFsplash10-003r-0009000000-afd2b610664571fce2e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 40V, Positive-QTOFsplash10-0udr-0139000000-00e46931cd7a9837ecfa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 10V, Negative-QTOFsplash10-004i-0009000000-8e501f86a47e1d657eea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 20V, Negative-QTOFsplash10-004i-0009000000-c6eaeed92493c892bd4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-O-Methylglycyrol 40V, Negative-QTOFsplash10-01sj-2259000000-6e9f4d6755f3c516acbb2021-09-22Wishart 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 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
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.. .