CHEBI:68914 - (16α,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-β-Dglucopyranoside

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ChEBI Name (16α,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-β-Dglucopyranoside
ChEBI ID CHEBI:68914
ChEBI ASCII Name (16alpha,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-beta-Dglucopyranoside
Definition A triterpenoid saponin of the class of cucurbitane glycosides isolated from Machilus yaoshansis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB8256546, eMolecules:885949, ZINC000002037537
Download Molfile XML SDF
Formula C33H44O11
Net Charge 0
Average Mass 616.69590
Monoisotopic Mass 616.28836
InChI InChI=1S/C33H44O11/c1-29(2)15-7-8-20-30(3)12-17(35)26(33(6)21(36)9-10-42-33)31(30,4)13-22(37)32(20,5)16(15)11-18(27(29)41)43-28-25(40)24(39)23(38)19(14-34)44-28/h7,9-11,16-17,19-20,23-26,28,34-35,38-40H,8,12-14H2,1-6H3/t16-,17-,19-,20+,23-,24+,25-,26+,28-,30+,31-,32+,33+/m1/s1
InChIKey WBITZIQWEJYFNO-GSNQANGESA-N
SMILES C[C@@]1(OC=CC1=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.
(via (16alpha,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-beta-Dglucopyranoside )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (16α,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-β-Dglucopyranoside (CHEBI:68914) has role plant metabolite (CHEBI:76924)
(16α,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-β-Dglucopyranoside (CHEBI:68914) is a β-D-glucoside (CHEBI:22798)
(16α,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-β-Dglucopyranoside (CHEBI:68914) is a furans (CHEBI:24129)
(16α,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-β-Dglucopyranoside (CHEBI:68914) is a monosaccharide derivative (CHEBI:63367)
(16α,20R)-20,24-epoxy-2,16-dihydroxy-25,26,27-trinorcucurbita-1,5,23-triene-3,11,22-trione 2-O-β-Dglucopyranoside (CHEBI:68914) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(4R,9β,16α)-16-hydroxy-9,10,14-trimethyl-1,11,22-trioxo-20,24-epoxy-4,9-cyclo-9,10-secochola-2,5,23-trien-2-yl β-D-glucopyranoside
Registry Number Type Source
22123600 Reaxys Registry Number Reaxys
Citation Type Source
22044245 PubMed citation Europe PMC
Last Modified
09 January 2014