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CHEBI:67294 - 3-acetyl-7-tigloylvilasinin lactone

ChEBI IDCHEBI:67294
ChEBI Name3-acetyl-7-tigloylvilasinin lactone
Stars
DefinitionA limonoid found in Azadirachta indica.
Last Modified18 November 2013
DownloadsMolfile
FormulaC33H44O9
Net Charge0
Average Mass584.706
Monoisotopic Mass584.29853
SMILES[H][C@]1([C@]2([H])C(=O)C=C3[C@@]2(C)CC[C@]2([H])[C@@]4(C)[C@@H](O)C[C@@H](OC(C)=O)[C@@]5(C)CO[C@@]([H])([C@@H](OC(=O)/C(C)=C/C)[C@@]32C)[C@]45[H])COC(=O)C1
InChIInChI=1S/C33H44O9/c1-8-16(2)29(38)42-28-26-27-31(5,15-40-26)23(41-17(3)34)13-22(36)33(27,7)20-9-10-30(4)21(32(20,28)6)12-19(35)25(30)18-11-24(37)39-14-18/h8,12,18,20,22-23,25-28,36H,9-11,13-15H2,1-7H3/b16-8+/t18-,20+,22+,23-,25-,26-,27+,28-,30-,31-,32-,33+/m1/s1
InChIKeyGWJBUONEPKDYGS-PPADEWLJSA-N
Species of MetaboliteComponentSourceComments
Azadirachta indica (ncbitaxon:124943) seed (BTO:0001226) PubMed (21381696) Defatted MeOH extract of seeds
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.
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)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) has functional parent tiglic acid (CHEBI:9592)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) has role metabolite (CHEBI:25212)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) has role plant metabolite (CHEBI:76924)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) is a acetate ester (CHEBI:47622)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) is a butan-4-olide (CHEBI:22950)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) is a limonoid (CHEBI:39434)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) is a pentacyclic triterpenoid (CHEBI:25872)
3-acetyl-7-tigloylvilasinin lactone (CHEBI:67294) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,3R,3aR,5aR,6S,6aR,9S,9aS,11aR,11bR,11cR)-3-(acetyloxy)-1-hydroxy-3a,6a,9a,11b-tetramethyl-8-oxo-9-[(3S)-5-oxotetrahydrofuran-3-yl]-1,2,3,3a,4,5a,6,6a,8,9,9a,10,11,11a,11b,11c-hexadecahydrocyclopenta[7,8]phenanthro[10,1-bc]furan-6-yl (2E)-2-methylbut-2-enoate
Registry NumbersSources
Reaxys:5198141Reaxys
Citations