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

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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)
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