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CHEBI:68370 - trichanolide

ChEBI IDCHEBI:68370
ChEBI Nametrichanolide
Stars
DefinitionA limonoid based on a mexicanolide-type skeleton isolated from Trichilia connaroides.
Last Modified7 February 2018
DownloadsMolfile
FormulaC32H42O10
Net Charge0
Average Mass586.678
Monoisotopic Mass586.27780
SMILES[H][C@@]12CC(=O)O[C@@H](c3ccoc3)[C@]1(C)CC[C@@]1([H])[C@@]23O[C@]3([H])[C@]2(O)C(=O)[C@@]1(C)[C@@H](CC(=O)OC)C(C)(C)[C@@H]2OC(=O)C(C)CC
InChIInChI=1S/C32H42O10/c1-8-16(2)24(35)41-26-28(3,4)19(13-21(33)38-7)30(6)18-9-11-29(5)20(32(18)27(42-32)31(26,37)25(30)36)14-22(34)40-23(29)17-10-12-39-15-17/h10,12,15-16,18-20,23,26-27,37H,8-9,11,13-14H2,1-7H3/t16?,18-,19+,20-,23+,26+,27-,29-,30-,31+,32-/m1/s1
InChIKeyQTIFIEXYFZYUMD-FIZZZUNNSA-N
Species of MetaboliteComponentSourceComments
Trichilia connaroides (IPNI:579388-1) leaf (BTO:0000713) PubMed (21268637) Methanolic extract of air-dried, powdered leaves
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
trichanolide (CHEBI:68370) has functional parent 2-methylbutyric acid (CHEBI:37070)
trichanolide (CHEBI:68370) has role plant metabolite (CHEBI:76924)
trichanolide (CHEBI:68370) is a bridged compound (CHEBI:35990)
trichanolide (CHEBI:68370) is a furans (CHEBI:24129)
trichanolide (CHEBI:68370) is a limonoid (CHEBI:39434)
trichanolide (CHEBI:68370) is a methyl ester (CHEBI:25248)
trichanolide (CHEBI:68370) is a organic heteropentacyclic compound (CHEBI:38164)
trichanolide (CHEBI:68370) is a tertiary α-hydroxy ketone (CHEBI:139592)
trichanolide (CHEBI:68370) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4R,4aR,6aR,7S,8S,10S,11S,11aR,12aS,12bR)-4-(furan-3-yl)-11-hydroxy-8-(2-methoxy-2-oxoethyl)-4a,7,9,9-tetramethyl-2,13-dioxododecahydro-2H,4H-7,11-methanooxireno[1,8]cycloocta[1,2-f]isochromen-10-yl 2-methylbutanoate
Registry NumbersSources
Reaxys:21299037Reaxys
Citations