CHEBI:68911 - (16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside

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ChEBI Name (16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside
ChEBI ID CHEBI:68911
ChEBI ASCII Name (16alpha,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-beta-D-glucopyranoside
Definition A triterpenoid saponin that is cucurbita-1,5-diene substituted by hydroxy groups at positions 16, 20 and 25, a methoxy group at position 24, oxo groups at positions 3, 11 and 22 and a β-D-glucopyranosyloxy residue at position 2. It has been isolated from the roots of Machilus yaoshansis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C37H56O13
Net Charge 0
Average Mass 708.83270
Monoisotopic Mass 708.37209
InChI InChI=1S/C37H56O13/c1-32(2)17-10-11-22-34(5)14-19(39)29(37(8,47)23(40)13-25(48-9)33(3,4)46)35(34,6)15-24(41)36(22,7)18(17)12-20(30(32)45)49-31-28(44)27(43)26(42)21(16-38)50-31/h10,12,18-19,21-22,25-29,31,38-39,42-44,46-47H,11,13-16H2,1-9H3/t18-,19-,21-,22+,25+,26-,27+,28-,29+,31-,34+,35-,36+,37+/m1/s1
InChIKey VFYMEDSYUASGPF-WLPFVFARSA-N
SMILES CO[C@@H](CC(=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)C(C)(C)O
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.
(via (16alpha,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-beta-D-glucopyranoside )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside (CHEBI:68911) has role plant metabolite (CHEBI:76924)
(16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside (CHEBI:68911) is a β-D-glucoside (CHEBI:22798)
(16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside (CHEBI:68911) is a cucurbitacin (CHEBI:16219)
(16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside (CHEBI:68911) is a monosaccharide derivative (CHEBI:63367)
(16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside (CHEBI:68911) is a tertiary α-hydroxy ketone (CHEBI:139592)
(16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside (CHEBI:68911) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(4R,9β,16α,24S)-16,20,25-trihydroxy-24-methoxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5-dien-2-yl β-D-glucopyranoside
Registry Number Type Source
22123604 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22044245 PubMed citation Europe PMC
Last Modified
06 February 2018