(16alpha,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-beta-D-glucopyranoside (CHEBI:68908)

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CHEBI:68908 - (16α,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside

ChEBI ID	CHEBI:68908
ChEBI Name	(16α,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside
Stars
ASCII Name	(16alpha,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-beta-D-glucopyranoside
Definition	A triterpenoid saponin of the class of cucurbitane glycosides isolated from the roots of Machilus yaoshansis. It has been shown to exhibit inhibitory activity against protein tyrosine phosphatase.
Last Modified	9 January 2014
Downloads	Molfile

Formula	C36H52O13
Net Charge	0
Average Mass	692.799
Monoisotopic Mass	692.34079
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@@]2([H])O[C@@]3(O)CC(C)(C)O[C@@]3(O)[C@](C)(O)[C@]12[H]
InChI	InChI=1S/C36H52O13/c1-29(2)15-35(44)36(45,49-29)34(8,43)26-19(48-35)12-31(5)21-10-9-16-17(33(21,7)22(38)13-32(26,31)6)11-18(27(42)30(16,3)4)46-28-25(41)24(40)23(39)20(14-37)47-28/h9,11,17,19-21,23-26,28,37,39-41,43-45H,10,12-15H2,1-8H3/t17-,19-,20-,21+,23-,24+,25-,26+,28-,31+,32-,33+,34-,35+,36+/m1/s1
InChIKey	ANFGZMJFIDODOI-JOWNWPMHSA-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.

EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor which interferes with the activity of the enzyme protein tyrosine phosphatases (PTPs), EC 3.1.3.48, involved in the removal of phosphate groups from phosphorylated tyrosine residues on proteins.

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,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside (CHEBI:68908) has role EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor (CHEBI:35608)
	(16α,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside (CHEBI:68908) has role plant metabolite (CHEBI:76924)
	(16α,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside (CHEBI:68908) is a hexacyclic triterpenoid (CHEBI:70994)
	(16α,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside (CHEBI:68908) is a monosaccharide derivative (CHEBI:63367)
	(16α,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside (CHEBI:68908) is a triterpenoid saponin (CHEBI:61778)
	(16α,20R,22S,23S)-16,23:22,25-diepoxy-2,20,22,23-tetrahydroxycucurbita-1,5-diene-3,11-dione 2-O-β-D-glucopyranoside (CHEBI:68908) is a β-D-glucoside (CHEBI:22798)

IUPAC Name
(4aR,4bR,6aR,6bR,7R,7aS,10aS,11aR,12aS,12bS)-7,7a,10a-trihydroxy-1,1,4b,6a,7,9,9,12a-octamethyl-2,5-dioxo-1,2,4a,4b,5,6,6a,6b,7,7a,9,10,10a,11a,12,12a,12b,13-octadecahydrofuro[3,2-b]naphtho[2',1':4,5]indeno[1,2-e]pyran-3-yl β-D-glucopyranoside

Registry Numbers	Sources
Reaxys:22123603	Reaxys

Citations