Record Information
Version1.0
Creation date2010-04-08 22:09:59 UTC
Update date2019-11-26 03:06:07 UTC
Primary IDFDB012075
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlycyrol
DescriptionGlycyrol, also known as neoglycyrol, 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. Glycyrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycyrol has been detected, but not quantified in, root vegetables. This could make glycyrol a potential biomarker for the consumption of these foods.
CAS Number23013-84-5
Structure
Thumb
Synonyms
SynonymSource
1,9-Dihydroxy-3-methoxy-2-prenylcoumestanChEBI
NeoglycyrolChEBI
3,9-Dihydroxy-1-methoxy-2-prenylcoumestanHMDB
Glycyroldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP4.06ALOGPS
logP3.97ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.03ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.33 m³·mol⁻¹ChemAxon
Polarizability38.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H18O6
IUPAC name5,14-dihydroxy-3-methoxy-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
InChI IdentifierInChI=1S/C21H18O6/c1-10(2)4-6-12-14(23)9-16-18(19(12)25-3)20-17(21(24)27-16)13-7-5-11(22)8-15(13)26-20/h4-5,7-9,22-23H,6H2,1-3H3
InChI KeyLWESBHWAOZORCQ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(CC=C(C)C)C(O)=CC2=C1C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2
Average Molecular Weight366.364
Monoisotopic Molecular Weight366.110338308
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
  • Benzofuran
  • Furopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.85%; H 4.95%; O 26.20%DFC
Melting PointMp 243.5-245°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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-1129000000-4b993b33166cb8fbdde8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-002k-2040900000-e8542ceec5c4a158aaeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-78e48e684af3992efae3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-2009000000-559fde7e518d612551bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-9353000000-cbb9dd6f93c1a2e64277JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-a33d47de2f3004d70f99JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0019000000-c6efce8ed6331ff56feaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067i-1965000000-11a2427325da7ae4a8f8JSpectraViewer
ChemSpider ID4478245
ChEMBL IDCHEMBL132695
KEGG Compound IDC16968
Pubchem Compound ID5320083
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33882
CRC / DFC (Dictionary of Food Compounds) IDHFR61-F:HCZ11-J
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009777
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference