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

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ChEBI Name cucurbitacin E 2-O-β-D-glucopyranoside
ChEBI ID CHEBI:68916
ChEBI 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C38H54O13
Net Charge 0
Average Mass 718.82760
Monoisotopic Mass 718.35644
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
SMILES CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C
Metabolite of Species Details
Machilus yaoshansis (NCBI:txid251260) Found in root (BTO:0001188). Ethanolic extract of air-dried and powdered roots 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.
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.
(via cucurbitacin )
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 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 β-D-glucoside (CHEBI:22798)
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)
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 Number Type Source
6628057 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22044245 PubMed citation Europe PMC
Last Modified
07 February 2018