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CHEBI:15939 - glycyrrhizinic acid

Default Structure
ChEBI IDCHEBI:15939
ChEBI Nameglycyrrhizinic acid
Stars
DefinitionA triterpenoid saponin that is the glucosiduronide derivative of 3β-hydroxy-11-oxoolean-12-en-30-oic acid.
Secondary ChEBI IDsCHEBI:5508, CHEBI:24418
Last Modified9 December 2024
DownloadsMolfile
FormulaC42H62O16
Net Charge0
Average Mass822.942
Monoisotopic Mass822.40379
SMILES[H][C@]12C(=O)C=C3[C@]4([H])C[C@@](C)(C(=O)O)CC[C@]4(C)CC[C@@]3(C)[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O[C@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]21C
InChIInChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1
InChIKeyLPLVUJXQOOQHMX-QWBHMCJMSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Glycyrrhiza (ncbitaxon:46347) - DOI (10.1021/np100371k)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.4.21.5 (thrombin) inhibitor  An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of thrombin (EC 3.4.21.5).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
glycyrrhizinic acid (CHEBI:15939) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
glycyrrhizinic acid (CHEBI:15939) has role plant metabolite (CHEBI:76924)
glycyrrhizinic acid (CHEBI:15939) is a enone (CHEBI:51689)
glycyrrhizinic acid (CHEBI:15939) is a glucosiduronic acid (CHEBI:24302)
glycyrrhizinic acid (CHEBI:15939) is a pentacyclic triterpenoid (CHEBI:25872)
glycyrrhizinic acid (CHEBI:15939) is a tricarboxylic acid (CHEBI:27093)
glycyrrhizinic acid (CHEBI:15939) is a triterpenoid saponin (CHEBI:61778)
glycyrrhizinic acid (CHEBI:15939) is conjugate acid of glycyrrhizinate(3−) (CHEBI:29807)
Incoming Relation(s)
glycyrrhizinate(3−) (CHEBI:29807) is conjugate base of glycyrrhizinic acid (CHEBI:15939)
IUPAC Name 
30-hydroxy-11,30-dioxoolean-12-en-3β-yl (2-O-β-D-glucopyranosyluronic acid)-α-D-glucopyranosiduronic acid
Synonyms  Source
(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acidChemIDplus
Glycyrrhizic acidKEGG COMPOUND
GlycyrrhizinKEGG COMPOUND
Manual XrefsDatabases
1325DrugCentral
C02284KEGG COMPOUND
GlycyrrhizinWikipedia
GLYCYRRHIZINATEMetaCyc
HMDB0029843HMDB
LMPR0106150013LIPID MAPS
Registry NumbersSources
Reaxys:77922Reaxys
CAS:1405-86-3KEGG COMPOUND
CAS:1405-86-3ChemIDplus
Citations