cucurbitacin E 2-O-beta-D-glucopyranoside (CHEBI:68916)

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CHEBI:68916 - cucurbitacin E 2-O-β-D-glucopyranoside

ChEBI ID	CHEBI:68916
ChEBI Name	cucurbitacin E 2-O-β-D-glucopyranoside
Stars
ASCII Name	cucurbitacin E 2-O-beta-D-glucopyranoside
Definition	A triterpenoid saponin that is cucurbitacin E attached to a β-D-glucopyranosyl residue at position 2 via a glycosidic linkage. Isolated from Machilus yaoshansis it exhibits antineoplastic activity.
Last Modified	7 February 2018
Downloads	Molfile

Formula	C38H54O13
Net Charge	0
Average Mass	718.837
Monoisotopic Mass	718.35644
SMILES	[H][C@@]12CC=C3C(C)(C)C(=O)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C[C@@]3([H])[C@]1(C)C(=O)C[C@@]1(C)[C@@]2(C)C[C@@H](O)[C@]1([H])[C@@](C)(O)C(=O)/C=C/C(C)(C)OC(C)=O
InChI	InChI=1S/C38H54O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-14,20-21,23-24,27-30,32,39,41,44-46,48H,11,15-17H2,1-9H3/b13-12+/t20-,21-,23-,24+,27-,28+,29-,30+,32-,35+,36-,37+,38+/m1/s1
InChIKey	QKEJRKXVLGOJMB-YYBMGDPWSA-N

Species of Metabolite	Component	Source	Comments
Machilus yaoshansis (ncbitaxon:251260)	root (BTO:0001188)	PubMed (22044245)	Ethanolic extract of air-dried and powdered roots

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.

allelochemical A class of secondary metabolites developed by many plants to influence the behaviour, growth or survival of herbivores, and thus acting as a defence against herbivory.

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)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) has functional parent cucurbitacin E (CHEBI:3944)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) has role antineoplastic agent (CHEBI:35610)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) has role plant metabolite (CHEBI:76924)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) is a acetate ester (CHEBI:47622)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) is a cucurbitacin (CHEBI:16219)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) is a monosaccharide derivative (CHEBI:63367)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) is a tertiary α-hydroxy ketone (CHEBI:139592)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) is a triterpenoid saponin (CHEBI:61778)
	cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) is a β-D-glucoside (CHEBI:22798)

IUPAC Name
(4R,9β,16α,23E)-2-(β-D-glucopyranosyloxy)-16,20-dihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate

Registry Numbers	Sources
Reaxys:6628057	Reaxys

Citations