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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0217900000-aadc516f5cfd224a8c71View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-0000192000-c460e8d231076de78a05View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000930000-25139768b4507e334b4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0000930000-25139768b4507e334b4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00or-0000900000-ada4fdd603d1852beae8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0000900000-276dcd237f3df1b55bf7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0000911000-952bbb171fba142dba69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014u-0000700009-50048523dd30a3c69126View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014u-0000700009-50048523dd30a3c69126View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0000900000-125f02720b2a01ba256eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0000900000-6466c540accc2a7ad380View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00or-0000900000-ada4fdd603d1852beae8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0000900000-276dcd237f3df1b55bf7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0000911000-952bbb171fba142dba69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014u-0000700009-50048523dd30a3c69126View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0000900000-c50958d1a751bbfbca79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dj-9781100000-4553bbbe9a30a0391bb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0000900000-027d29bdfec0cb682eabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0000900000-7d4a004adc92eda07905View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0000900000-04e795c32f4f79f139f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a6r-0004900000-5d9468128c8fc0642c7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-9677a3bedc1d92d76314View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pdr-0001900000-29bf26f4b3b6b73752a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-1609800000-2dedffb68814f07143d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-612624a459b00afd684cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kxr-0000900000-6cf44557b5b0900d64eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-1001900000-918ef5666b6581adc583View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
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