madecassoside (CHEBI:66651)

EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66651 - madecassoside

Take structure to advanced search

ChEBI ID	CHEBI:66651
ChEBI Name	madecassoside
Stars
Definition	A triterpenoid saponin that is a trisaccharide derivative of madecassic acid. Isolated from Centella asiatica, it exhibits anti-inflammatory, antioxidant and antirheumatic activities.
Last Modified	16 April 2025
Downloads	Molfile

Formula	C48H78O20
Net Charge	0
Average Mass	975.132
Monoisotopic Mass	974.50864
SMILES	[H][C@@]1(O[C@H]2[C@H](O)[C@@H](O)[C@H](OC[C@H]3O[C@@H](OC(=O)[C@]45CC[C@@H](C)[C@H](C)[C@@]4([H])C4=CC[C@]6([H])[C@@]7(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@]7([H])[C@H](O)C[C@@]6(C)[C@]4(C)CC5)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H]2CO)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
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
InChIKey	BNMGUJRJUUDLHW-HCZMHFOYSA-N

Species of Metabolite	Component	Source	Comments
Centella asiatica (ncbitaxon:48106)	-	PubMed (18484522)

Roles Classification

Chemical Role:	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:	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.
Applications:	antirheumatic drug A drug used to treat rheumatoid arthritis. anti-inflammatory agent Any compound that has anti-inflammatory effects. vulnerary A drug used in treating and healing of wounds.

ChEBI Ontology

Outgoing Relation(s)
	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)

IUPAC Name
6-deoxy-α-L-mannopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-1-O-[(2α,3β,6β)-2,3,6,23-tetrahydroxy-28-oxours-12-en-28-yl]-β-D-glucopyranose

Synonyms	Source
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
asiaticoside A	ChEBI

UniProt Name	Source
madecassoside	UniProt

Manual Xrefs	Databases
KR20110132629	Patent

Registry Numbers	Sources
Reaxys:9113695	Reaxys
CAS:34540-22-2	ChemIDplus

Citations