CHEBI:15939 - glycyrrhizinic acid

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ChEBI Name glycyrrhizinic acid
ChEBI ID CHEBI:15939
Definition A triterpenoid saponin that is the glucosiduronide derivative of 3β-hydroxy-11-oxoolean-12-en-30-oic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5508, CHEBI:24418
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Formula C42H62O16
Net Charge 0
Average Mass 822.93210
Monoisotopic Mass 822.404
InChI InChI=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
InChIKey LPLVUJXQOOQHMX-QWBHMCJMSA-N
SMILES [H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C(O)=O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O
Metabolite of Species Details
Glycyrrhiza (NCBI:46347) See: DOI
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl-2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid ChemIDplus
Glycyrrhizic acid KEGG COMPOUND
glycyrrhizic acid UniProt
Glycyrrhizin KEGG COMPOUND
Database Links Databases
C02284 KEGG COMPOUND
Glycyrrhizin Wikipedia
GLYCYRRHIZINATE MetaCyc
HMDB29843 HMDB
LMPR0106150013 LIPID MAPS
View more database links
Registry Numbers Types Sources
1405-86-3 CAS Registry Number KEGG COMPOUND
1405-86-3 CAS Registry Number ChemIDplus
77922 Beilstein Registry Number Beilstein
77922 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11282481 PubMed citation Europe PMC
15013279 PubMed citation Europe PMC
24497916 PubMed citation Europe PMC
Last Modified
17 February 2014