beta-Glycyrrhetinic acid (CHEM028545)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:31:51 UTC
Update Date2016-11-09 01:18:42 UTC
Accession NumberCHEM028545
Identification
Common Namebeta-Glycyrrhetinic acid
ClassSmall Molecule
Descriptionbeta-Glycyrrhetinic acid is found in herbs and spices. beta-Glycyrrhetinic acid is a constituent of licorice (Glycyrrhiza glabra) root
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
b-GlycyrrhetinateGenerator
b-Glycyrrhetinic acidGenerator
beta-GlycyrrhetinateGenerator
Β-glycyrrhetinateGenerator
Β-glycyrrhetinic acidGenerator
18alpha-GAMeSH
18beta-GAMeSH
18beta-Glycyrrhetinic acidMeSH
18 alpha-Glycyrrhetinic acidHMDB
18-Isoglycyrrhetinic acidHMDB
18a-Glycyrrhetic acidHMDB
18alpha-Olean-12-en-30-Oic acid, 3beta-hydroxy-11-oxo- (6ci,7ci,8ci)HMDB
3-Hydroxy-11-oxo-(3beta,18alpha,20beta)-olean-12-en-29-Oic acidHMDB
Isoglycyrrhetinic acidHMDB
18a-GlycyrrhetinateGenerator
18a-Glycyrrhetinic acidGenerator
18alpha-GlycyrrhetinateGenerator
18Α-glycyrrhetinateGenerator
18Α-glycyrrhetinic acidGenerator
Chemical FormulaC30H46O4
Average Molecular Mass470.684 g/mol
Monoisotopic Mass470.340 g/mol
CAS Registry Number1449-05-4
IUPAC Name(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-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 Name(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid
SMILES[H][C@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O
InChI IdentifierInChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21+,22+,23-,26-,27+,28+,29-,30-/m1/s1
InChI KeyMPDGHEJMBKOTSU-PMTKVOBESA-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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 Solubility0.0017 g/LALOGPS
logP5.45ALOGPS
logP6.03ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.27 m³·mol⁻¹ChemAxon
Polarizability55.39 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0216900000-74f3465dcca9019ca951Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-1021592000-56e1df4c4a6a4d9460ddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0000900000-3483213eb90b7762fb72Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0000900000-5fa2c06264507f4f3c15Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0342900000-10ea26e7f92faaef6f2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-05i0-0920100000-2d3223a633769dc0e638Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000900000-9e7d44415d3a88016d9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-b9d584487d89a81e7f29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000900000-4fd1d9106fe4e18c8fa4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-0101900000-219872d2c000651a313bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-2908700000-29dd3e801a0b370c5cf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-f48f58fd0b19d7113d85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0690-0000900000-dd269ff3ff161d041badSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-1001900000-473216311a73be4966f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-d60788820b8857f5a5d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-d60788820b8857f5a5d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-2000900000-2ccd14915fa2a3e27d8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-296f14837562a59678caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-0001900000-0227108f5ac33bae6da3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-4329000000-15bb26ca9bcb86b1f04eSpectrum
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 IDHMDB0034517
FooDB IDFDB013018
Phenol Explorer IDNot Available
KNApSAcK IDC00003521
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID66115
ChEBI IDNot Available
PubChem Compound ID73398
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