capilliposide B (CHEBI:65574)

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CHEBI:65574 - capilliposide B

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ChEBI ID	CHEBI:65574
ChEBI Name	capilliposide B
Stars
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.
Last Modified	4 September 2015
Downloads	Molfile

Formula	C58H96O24
Net Charge	0
Average Mass	1177.382
Monoisotopic Mass	1176.62915
SMILES	[H][C@@]1(O[C@H]2[C@H](O[C@@]3([H])CC[C@]4(C)[C@@]5([H])CC[C@@]67O[C@@H](O)[C@]8([C@H](O)C[C@@]6(C)[C@]5(C)CC[C@@]4([H])C3(C)C)[C@@H](OC(=O)CCCCC)CC(C)(C)C[C@]87[H])OC[C@]([H])(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@]3([H])OC[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
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

Species of Metabolite	Component	Source	Comments
Lysimachia capillipes (ncbitaxon:306310)	whole plant (BTO:0001461)	PubMed (16595968)

Roles Classification

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.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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 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)
	capilliposide B (CHEBI:65574) is a α-L-arabinopyranoside (CHEBI:37782)

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 Numbers	Sources
Reaxys:10416641	Reaxys

Citations