CHEBI:66652 - madhucoside A

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ChEBI Name madhucoside A
ChEBI ID CHEBI:66652
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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C69H112O34
Net Charge 0
Average Mass 1485.60720
Monoisotopic Mass 1484.70350
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
SMILES [H][C@]1(OC[C@](O)(CO)[C@H]1O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]1([H])O[C@H]1[C@@H](O)C[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@]5(CC[C@@]4(C)[C@]3(C)C[C@@H](O)[C@@]2([H])[C@]1(C)CO)C(=O)O[C@@H]1OC[C@H](O)[C@H](O)[C@@]1([H])O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@@]1([H])O[C@@H]1OC[C@@H](O)[C@H](O[C@@]2([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@@]1([H])O[C@@H]1OC[C@](C)(CO)[C@H]1O
Metabolite of Species Details
Madhuca indica (NCBI:txid571269) Found in bark (BTO:0001301). See: PubMed
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
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.
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 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
Citation Waiting for Citations Type Source
15104500 PubMed citation Europe PMC
Last Modified
20 January 2014