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Record Information
Version3.6
Creation Date2009-01-30 10:07:36 UTC
Update Date2016-02-11 01:21:49 UTC
HMDB IDHMDB11628
Secondary Accession NumbersNone
Metabolite 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 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 (Chandler,1985). 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 (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
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
GlycyrrhetinateHMDB
Glycyrrhetinic acidHMDB
Uralenic acidHMDB
Chemical FormulaC30H46O4
Average Molecular Weight470.6838
Monoisotopic Molecular Weight470.33960996
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 KeyInChIKey=MPDGHEJMBKOTSU-WFJWTYAKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oleanane triterpenoids. These are triterpenoids with a structure based on the oleanane skeleton, an 4,4,6a,8a,11,14b-heptamethyl-hexadecahydropicene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentOleanane triterpenoids
Alternative Parents
Substituents
  • Oleanane triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point296 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.27 m3·mol-1ChemAxon
Polarizability55.38 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.104 +/- 0.008 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB020713
KNApSAcK IDC00003521
Chemspider ID17930566
KEGG Compound IDC02283
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlycyrrhetinic acid
NuGOwiki LinkHMDB11628
Metagene LinkHMDB11628
METLIN IDNot Available
PubChem Compound18526330
PDB IDNot Available
ChEBI ID30853
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:
HSD11B2
Uniprot ID:
P80365
Molecular weight:
44126.06