madhucoside A (CHEBI:66652)

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CHEBI:66652 - madhucoside A

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ChEBI ID	CHEBI:66652
ChEBI Name	madhucoside A
Stars
Definition	A triterpenoid saponin that consists of protobassic acid as the aglycone moiety. Isolated from the barks of Madhuca indica, it exhibits radical scavenging activity.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C69H112O34
Net Charge	0
Average Mass	1485.621
Monoisotopic Mass	1484.70350
SMILES	[H][C@]1(O[C@H]2[C@H](O)CO[C@@H](O[C@@]3([H])[C@H](O[C@@]4([H])[C@H](OC(=O)[C@]56CCC(C)(C)C[C@@]5([H])C5=CC[C@]7([H])[C@@]8(C)C[C@H](O)[C@H](O[C@]9([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O[C@]9([H])OC[C@](O)(CO)[C@H]9O)[C@@](C)(CO)[C@]8([H])[C@H](O)C[C@@]7(C)[C@]5(C)CC6)OC[C@H](O)[C@@H]4O)O[C@@H](C)[C@H](O)[C@H]3O)[C@]2([H])O[C@@H]2OC[C@](C)(CO)[C@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChI	InChI=1S/C69H112O34/c1-27-37(78)41(82)44(85)54(94-27)97-45-34(77)21-91-56(49(45)101-59-51(86)63(5,22-71)25-92-59)98-47-42(83)38(79)28(2)95-57(47)99-46-39(80)33(76)20-90-55(46)103-61(88)68-14-12-62(3,4)16-30(68)29-10-11-36-64(6)17-32(75)53(65(7,23-72)50(64)31(74)18-67(36,9)66(29,8)13-15-68)102-58-48(43(84)40(81)35(19-70)96-58)100-60-52(87)69(89,24-73)26-93-60/h10,27-28,30-60,70-87,89H,11-26H2,1-9H3/t27-,28-,30-,31+,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+,43-,44+,45-,46+,47+,48+,49+,50+,51-,52-,53-,54+,55-,56-,57-,58-,59-,60-,63-,64+,65-,66+,67+,68-,69+/m0/s1
InChIKey	BKOFXNDZBMIYRU-UHRQVOEYSA-N

Species of Metabolite	Component	Source	Comments
Madhuca indica (ncbitaxon:571269)	bark (BTO:0001301)	PubMed (15104500)

Roles Classification

Chemical Role:	radical scavenger A role played by a substance that can react readily with, and thereby eliminate, radicals.
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.

ChEBI Ontology

Outgoing Relation(s)
	madhucoside A (CHEBI:66652) has functional parent protobassic acid (CHEBI:73086)
	madhucoside A (CHEBI:66652) has role plant metabolite (CHEBI:76924)
	madhucoside A (CHEBI:66652) has role radical scavenger (CHEBI:48578)
	madhucoside A (CHEBI:66652) is a carboxylic ester (CHEBI:33308)
	madhucoside A (CHEBI:66652) is a pentacyclic triterpenoid (CHEBI:25872)
	madhucoside A (CHEBI:66652) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
6-deoxy-β-L-mannopyranosyl-(1→3)-2-O-[(2S,3R,4S)-3-hydroxy-4-(hydroxymethyl)-4-methyltetrahydrofuran-2-yl]-β-D-xylopyranosyl-(1→2)-6-deoxy-α-L-mannopyranosyl-(1→2)-1-O-[(2β,3β,6β)-3-({2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-β-D-glucopyranosyl}oxy)-2,6,23-trihydroxy-28-oxoolean-12-en-28-yl]-α-L-arabinopyranose

Synonym	Source
3-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranosyl-28-O-{β-D-xylopyranosyl(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl}protobassic acid	ChEBI

Citations