28-Hydroxyglycyrrhetic acid (CHEM029176)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:59:11 UTC
Update Date2016-11-09 01:18:50 UTC
Accession NumberCHEM029176
Identification
Common Name28-Hydroxyglycyrrhetic acid
ClassSmall Molecule
Description28-Hydroxyglycyrrhetic acid is found in herbs and spices. 28-Hydroxyglycyrrhetic acid is isolated from Glycyrrhiza glabra (licorice).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
28-HydroxyglycyrrhetateGenerator
10-Hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylateHMDB
Chemical FormulaC30H46O5
Average Molecular Mass486.683 g/mol
Monoisotopic Mass486.335 g/mol
CAS Registry Number56061-86-0
IUPAC Name10-hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
Traditional Name10-hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid
SMILESCC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C3CC(C)(CCC3(CO)CCC12C)C(O)=O
InChI IdentifierInChI=1S/C30H46O5/c1-25(2)21-7-10-29(6)23(27(21,4)9-8-22(25)33)20(32)15-18-19-16-26(3,24(34)35)11-13-30(19,17-31)14-12-28(18,29)5/h15,19,21-23,31,33H,7-14,16-17H2,1-6H3,(H,34,35)
InChI KeyCWCIIDUCIPKOCX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclohexenone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0037 g/LALOGPS
logP4.2ALOGPS
logP4.75ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity136.04 m³·mol⁻¹ChemAxon
Polarizability56.32 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abi-0103900000-bb4f3296f847ead3de5fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-1030329000-3fd777b1538bbc37ff81Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0000900000-f1278bf34e6e70d65cacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-0000900000-30105ce6302f2b462aa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-010r-3429800000-587433e6b08775bd8537Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-805de61cabdfc392f61cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05tu-0000900000-848d33776fc5d17f3f40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvr-1000900000-67ad3a0f7d4929e6dab9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-6a75a140e72d68a6c193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-2f3801df114d92826de5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0000900000-b2fa65e96fdfde13c335Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-016546413d32d1680053Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-0000900000-25888b11ff7f52f55afbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9488300000-0325b110c48d0896b186Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035259
FooDB IDFDB013920
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013887
ChEBI ID168613
PubChem Compound ID76064992
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM