CHEBI:66651 - madecassoside

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ChEBI Name madecassoside
Definition A triterpenoid saponin that is a trisaccharide derivative of madecassic acid. Isolated from Centella asiatica, it exhibits anti-inflammatory, antioxidant and antirheumatic activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C48H78O20
Net Charge 0
Average Mass 975.12090
Monoisotopic Mass 974.50864
InChI InChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42+,44-,45+,46-,47-,48+/m1/s1
SMILES [H][C@]1(O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)O[C@@H]1[C@@H](CO)O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@]34CC[C@@H](C)[C@H](C)[C@@]3([H])C3=CC[C@]5([H])[C@@]6(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@]6([H])[C@H](O)C[C@@]5(C)[C@]3(C)CC4)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O
Metabolite of Species Details
Centella asiatica (NCBI:txid48106) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
A drug used in treating and healing of wounds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing madecassoside (CHEBI:66651) has functional parent madecassic acid (CHEBI:73058)
madecassoside (CHEBI:66651) has parent hydride ursane (CHEBI:35711)
madecassoside (CHEBI:66651) has role anti-inflammatory agent (CHEBI:67079)
madecassoside (CHEBI:66651) has role antioxidant (CHEBI:22586)
madecassoside (CHEBI:66651) has role antirheumatic drug (CHEBI:35842)
madecassoside (CHEBI:66651) has role plant metabolite (CHEBI:76924)
madecassoside (CHEBI:66651) has role vulnerary (CHEBI:73336)
madecassoside (CHEBI:66651) is a carboxylic ester (CHEBI:33308)
madecassoside (CHEBI:66651) is a pentacyclic triterpenoid (CHEBI:25872)
madecassoside (CHEBI:66651) is a trisaccharide derivative (CHEBI:63571)
madecassoside (CHEBI:66651) is a triterpenoid saponin (CHEBI:61778)
Synonyms Sources
asiaticoside A ChEBI
O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl(2α,3β,4α,6β)-2,3,6,23-tetrahydroxyurs-12-en-28-oate ChEBI
Manual Xref Database
KR20110132629 Patent
View more database links
Registry Numbers Types Sources
34540-22-2 CAS Registry Number ChemIDplus
9113695 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18484522 PubMed citation Europe PMC
19135346 PubMed citation Europe PMC
20143295 PubMed citation Europe PMC
22360962 PubMed citation Europe PMC
22829481 PubMed citation Europe PMC
Last Modified
20 January 2014