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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:39:18 UTC
Update Date2019-07-23 06:14:35 UTC
HMDB IDHMDB0033882
Secondary Accession Numbers
  • HMDB33882
Metabolite Identification
Common 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). Outside of the human body, glycyrol has been detected, but not quantified in, root vegetables. This could make glycyrol a potential biomarker for the consumption of these foods.
Structure
Data?1563862475
Synonyms
ValueSource
1,9-Dihydroxy-3-methoxy-2-prenylcoumestanChEBI
NeoglycyrolChEBI
3,9-Dihydroxy-1-methoxy-2-prenylcoumestanHMDB
Chemical FormulaC21H18O6
Average Molecular Weight366.364
Monoisotopic Molecular Weight366.110338308
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
Traditional 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
CAS Registry Number23013-84-5
SMILES
COC1=C(CC=C(C)C)C(O)=CC2=C1C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2
InChI Identifier
InChI=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
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
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point243.5 - 245 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-1129000000-4b993b33166cb8fbdde8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-002k-2040900000-e8542ceec5c4a158aaeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-78e48e684af3992efae3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-2009000000-559fde7e518d612551bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-9353000000-cbb9dd6f93c1a2e64277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-a33d47de2f3004d70f99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0019000000-c6efce8ed6331ff56feaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067i-1965000000-11a2427325da7ae4a8f8Spectrum
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 IDFDB012075
KNApSAcK IDC00009777
Chemspider ID4478245
KEGG Compound IDC16968
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320083
PDB IDNot Available
ChEBI ID80832
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shin EM, Zhou HY, Guo LY, Kim JA, Lee SH, Merfort I, Kang SS, Kim HS, Kim S, Kim YS: Anti-inflammatory effects of glycyrol isolated from Glycyrrhiza uralensis in LPS-stimulated RAW264.7 macrophages. Int Immunopharmacol. 2008 Nov;8(11):1524-32. doi: 10.1016/j.intimp.2008.06.008. Epub 2008 Jul 11. [PubMed:18621150 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .