lysikokianoside 1 (CHEBI:69611)

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CHEBI:69611 - lysikokianoside 1

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ChEBI ID	CHEBI:69611
ChEBI Name	lysikokianoside 1
Stars
Definition	A triterpenoid saponin that is (3β,16α)-13,28-epoxyoleanane-3,16-diol attached to a tetrasaccharide residue at position 3 via a glycosidic linkage. Isolated from aerial parts of Lysimachia clethroides, it exhibits antineoplastic activity.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C52H86O21
Net Charge	0
Average Mass	1047.239
Monoisotopic Mass	1046.56616
SMILES	[H][C@@]1(O[C@@H]2[C@@H](O)[C@@]([H])(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@]3([H])O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)CO[C@@]2([H])O[C@H]2CC[C@]3(C)[C@@]4([H])CC[C@]56OC[C@@]7(CCC(C)(C)C[C@]75[H])[C@H](O)C[C@@]6(C)[C@]4(C)CC[C@@]3([H])C2(C)C)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C52H86O21/c1-46(2)14-15-51-22-67-52(29(51)16-46)13-9-28-48(5)11-10-31(47(3,4)27(48)8-12-49(28,6)50(52,7)17-30(51)56)71-44-40(73-43-39(64)36(61)33(58)24(18-53)68-43)35(60)26(21-66-44)70-45-41(37(62)34(59)25(19-54)69-45)72-42-38(63)32(57)23(55)20-65-42/h23-45,53-64H,8-22H2,1-7H3/t23-,24-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,48+,49-,50+,51-,52+/m1/s1
InChIKey	GQENXAKENMICMF-UXYUNAJASA-N

Species of Metabolite	Component	Source	Comments
Lysimachia clethroides (ncbitaxon:167892)	aerial part (BTO:0001658)	PubMed (21928797)	Air-dried, powdered aerial parts were extracted with 70% aqueous ethyl alcohol.

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)
	lysikokianoside 1 (CHEBI:69611) has role antineoplastic agent (CHEBI:35610)
	lysikokianoside 1 (CHEBI:69611) has role plant metabolite (CHEBI:76924)
	lysikokianoside 1 (CHEBI:69611) is a cyclic ether (CHEBI:37407)
	lysikokianoside 1 (CHEBI:69611) is a hexacyclic triterpenoid (CHEBI:70994)
	lysikokianoside 1 (CHEBI:69611) is a secondary alcohol (CHEBI:35681)
	lysikokianoside 1 (CHEBI:69611) is a tetrasaccharide derivative (CHEBI:63567)
	lysikokianoside 1 (CHEBI:69611) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranoside

Synonym	Source
3β-O-{β-D-xylopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-{O-β-D-glucopyranosyl-(1→2)}-α-L-arabinopyranosyl}-16α-hydroxy-13β,28-epoxy oleanane	ChEBI

Registry Numbers	Sources
Reaxys:5714226	Reaxys

Citations