CHEBI:65574 - capilliposide B

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ChEBI Name capilliposide B
ChEBI ID CHEBI:65574
Definition A triterpenoid saponin that consists of anagalligenin A substituted by a caproyl group at position 22 and a β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl moiety at position 3 via a glycosidic linkage. It is isolated from the whole plants of Lysimachia capillipes and has been shown to exhibit potent cytotoxicity against human A-2780 cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C58H96O24
Net Charge 0
Average Mass 1177.36840
Monoisotopic Mass 1176.62915
InChI InChI=1S/C58H96O24/c1-9-10-11-12-36(63)78-35-21-52(2,3)19-32-57-18-14-31-54(6)16-15-34(53(4,5)30(54)13-17-55(31,7)56(57,8)20-33(62)58(32,35)51(72)82-57)79-49-45(81-48-44(71)41(68)38(65)27(22-59)75-48)40(67)29(25-74-49)77-50-46(42(69)39(66)28(23-60)76-50)80-47-43(70)37(64)26(61)24-73-47/h26-35,37-51,59-62,64-72H,9-25H2,1-8H3/t26-,27-,28-,29+,30+,31-,32+,33-,34+,35+,37+,38-,39-,40+,41+,42+,43-,44-,45-,46-,47+,48+,49+,50+,51-,54+,55-,56+,57+,58-/m1/s1
InChIKey QFCPRKADRIVFOU-CGWAXLKRSA-N
SMILES [H][C@@]1(CO[C@@H](O[C@@]2([H])CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])CC[C@@]35O[C@@H](O)[C@]6([C@H](O)C[C@@]43C)[C@H](CC(C)(C)C[C@@]56[H])OC(=O)CCCCC)C2(C)C)[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@]1([H])OC[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Lysimachia capillipes (NCBI:txid306310) Found in whole plant (BTO:0001461). See: PubMed
Roles Classification
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 )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing capilliposide B (CHEBI:65574) has functional parent anagalligenin A (CHEBI:71347)
capilliposide B (CHEBI:65574) has parent hydride oleanane (CHEBI:36481)
capilliposide B (CHEBI:65574) has role antineoplastic agent (CHEBI:35610)
capilliposide B (CHEBI:65574) has role plant metabolite (CHEBI:76924)
capilliposide B (CHEBI:65574) is a α-L-arabinopyranoside (CHEBI:37782)
capilliposide B (CHEBI:65574) is a bridged compound (CHEBI:35990)
capilliposide B (CHEBI:65574) is a cyclic ether (CHEBI:37407)
capilliposide B (CHEBI:65574) is a diol (CHEBI:23824)
capilliposide B (CHEBI:65574) is a hexacyclic triterpenoid (CHEBI:70994)
capilliposide B (CHEBI:65574) is a hexanoate ester (CHEBI:87656)
capilliposide B (CHEBI:65574) is a lactol (CHEBI:38131)
capilliposide B (CHEBI:65574) is a secondary alcohol (CHEBI:35681)
capilliposide B (CHEBI:65574) is a tetrasaccharide derivative (CHEBI:63567)
capilliposide B (CHEBI:65574) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β,16α,22α)-3-{[β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl]oxy}-16,28-dihydroxy-13,28-epoxyoleanan-22-yl hexanoate
Synonym Source
22-caproylanagalligenin A-3-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside ChEBI
Registry Number Type Source
10416641 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16595968 PubMed citation Europe PMC
Last Modified
04 September 2015