Showing metabocard for Glycyrrhetinic acid (BMDB0011628)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:21:58 UTC
Update Date2020-04-22 15:45:40 UTC
BMDB IDBMDB0011628
Secondary Accession Numbers
  • BMDB11628
Metabolite Identification
Common NameGlycyrrhetinic acid
DescriptionGlycyrrhetinic acid, also known as glycyrrhetinate or biosone, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Glycyrrhetinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 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 KeyMPDGHEJMBKOTSU-WFJWTYAKSA-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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011628
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020713
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Corticosteroid 11-beta-dehydrogenase isozyme 2
General function:
Lipid transport and metabolism
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. Affinity towards corticosterone is higher than cortisol or dexamethasone.
Gene Name:
HSD11B2
Uniprot ID:
O77667
Molecular weight:
43987.0