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Record Information
Version1.0
Created at2009-01-30 10:07:36 UTC
Updated at2021-08-19 23:58:52 UTC
NP-MRD IDNP0001174
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlycyrrhetinic acid
DescriptionGlycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was first obtained from the herb liquorice. It is used in flavouring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties (PMID:32106571 ). In glycyrrhetinic acid the functional group (R) is a hydroxyl group. Research in 2005 demonstrated that with a proper functional group a very effective glycyrrhetinic artificial sweetener can be obtained. When R is an anionic NHCO(CH2)CO2K side chain, the sweetening effect is found to 1200 times that of sugar (human sensory panel data). A shorter or longer spacer reduces the sweetening effect. One explanation is that the taste bud cell receptor has 1.3 Nanometers (13 angstroms) available for docking with the sweetener molecule. In addition the sweetener molecule requires three proton donor positions of which two reside at the extremities to be able to interact efficiently with the receptor cavity.
Structure
Thumb
Synonyms
ValueSource
GlycyrrhetinateGenerator
18b-Glycyrrhetic acidHMDB
18b-Glycyrrhetinic acidHMDB
18b-Glycyrrhtinic acidHMDB
3-Glycyrrhetinic acidHMDB
3-Hydroxy-11-oxoolean-12-en-29-OateHMDB
3-Hydroxy-11-oxoolean-12-en-29-Oic acidHMDB
3-Hydroxy-11-oxoolean-12-en-29-Oic acid (acd/name 4.0)HMDB
3b-Hydroxy-11-oxo-olean-12-en-30-OateHMDB
3b-Hydroxy-11-oxo-olean-12-en-30-Oic acidHMDB
3b-Hydroxy-11-oxoolean-12-en-30-OateHMDB
3b-Hydroxy-11-oxoolean-12-en-30-Oic acidHMDB
a-Glycyrrhetinic acidHMDB
alpha-Glycyrrhetinic acidHMDB
b-Glycyrrhetic acidHMDB
beta-Glycyrrhetic acidHMDB
BiosoneHMDB
EnoxoloneHMDB
Glycyrrhetic acidHMDB
GlycyrrhetinHMDB
Uralenic acidHMDB
Acid, glycyrrhetinicHMDB
Dexo brand OF glycyrrhetinic acidHMDB
Po 12HMDB
Rhetinic acidHMDB
Acid, glycyrrheticHMDB
Plantes et médecines brand OF glycyrrhetinic acidHMDB
Acid, rhetinicHMDB
Acid, uralenicHMDB
ArthrodontHMDB
GlyciramHMDB
GlycyramHMDB
JintanHMDB
(2S,4AS,6as,6BR,10S,12as)-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-carboxylateHMDB
12, PoHMDB
Glycyrrhetinic acidHMDB, MeSH
Chemical FormulaC30H46O4
Average Mass470.6838 Da
Monoisotopic Mass470.33961 Da
IUPAC Name(2S,4aS,6aS,6bR,10S,12aS)-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,10S,12aS)-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
CAS Registry Number471-53-4
SMILES
CC1(C)[C@@H](O)CC[C@@]2(C)C1CC[C@]1(C)C2C(=O)C=C2C3C[C@](C)(CC[C@]3(C)CC[C@@]12C)C(O)=O
InChI Identifier
InChI=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+/m0/s1
InChI KeyMPDGHEJMBKOTSU-WFJWTYAKSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Echinopora lamellosa
Glycyrrhiza asperaKNApSAcK Database
Glycyrrhiza glabraKNApSAcK Database
Glycyrrhiza inflataKNApSAcK Database
Glycyrrhiza kansuensisKNApSAcK Database
Glycyrrhiza radixKNApSAcK Database
Glycyrrhiza uralensisKNApSAcK Database
Glycyrrhiza yunnanensisKNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point296 °CNot Available
Boiling Point588.34 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.011 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.498 (est)The Good Scents Company Information System
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011628
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112304
KNApSAcK IDC00003521
Chemspider ID17930566
KEGG Compound IDC02283
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnoxolone
METLIN IDNot Available
PubChem Compound18526330
PDB IDNot Available
ChEBI ID30853
Good Scents IDrw1157421
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. El-Saber Batiha G, Magdy Beshbishy A, El-Mleeh A, Abdel-Daim MM, Prasad Devkota H: Traditional Uses, Bioactive Chemical Constituents, and Pharmacological and Toxicological Activities of Glycyrrhiza glabra L. (Fabaceae). Biomolecules. 2020 Feb 25;10(3). pii: biom10030352. doi: 10.3390/biom10030352. [PubMed:32106571 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.