clethroidoside D (CHEBI:69604)

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CHEBI:69604 - clethroidoside D

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ChEBI ID	CHEBI:69604
ChEBI Name	clethroidoside D
Stars
Definition	A triterpenoid saponin that is (3β)-3-hydroxy-13,28-epoxyoleanan-16-one attached to a tetrasaccharide residue at position 3 via a glycosidic linkage. Isolated from the aerial parts of Lysimachia clethroides, it exhibits antineoplastic activity.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C52H84O21
Net Charge	0
Average Mass	1045.223
Monoisotopic Mass	1044.55051
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(=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/C52H84O21/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/h23-29,31-45,53-55,57-64H,8-22H2,1-7H3/t23-,24-,25-,26+,27+,28-,29-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,48+,49-,50+,51-,52+/m1/s1
InChIKey	LXYNMISGVPYMHU-LGZUVIOGSA-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)
	clethroidoside D (CHEBI:69604) has parent hydride oleanane (CHEBI:36481)
	clethroidoside D (CHEBI:69604) has role antineoplastic agent (CHEBI:35610)
	clethroidoside D (CHEBI:69604) has role plant metabolite (CHEBI:76924)
	clethroidoside D (CHEBI:69604) is a cyclic ether (CHEBI:37407)
	clethroidoside D (CHEBI:69604) is a cyclic terpene ketone (CHEBI:36130)
	clethroidoside D (CHEBI:69604) is a hexacyclic triterpenoid (CHEBI:70994)
	clethroidoside D (CHEBI:69604) is a tetrasaccharide derivative (CHEBI:63567)
	clethroidoside D (CHEBI:69604) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
(3β)-16-oxo-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
3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl-13β,28-epoxy-3β-hydroxyolean-16-one	ChEBI

Registry Numbers	Sources
Reaxys:22007804	Reaxys

Citations