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

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CHEBI:68911 - (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 Name	(16α,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-β-D-glucopyranoside
Stars
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.
Last Modified	6 February 2018
Downloads	Molfile

Formula	C37H56O13
Net Charge	0
Average Mass	708.842
Monoisotopic Mass	708.37209
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@H](OC)C(C)(C)O
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

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.

ChEBI Ontology

Outgoing Relation(s)
	(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 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)
	(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)

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 Numbers	Sources
Reaxys:22123604	Reaxys

Citations