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CHEBI:67303 - 3-acetyl-11-methoxy-1-tigloylazadirachtinin

ChEBI IDCHEBI:67303
ChEBI Name3-acetyl-11-methoxy-1-tigloylazadirachtinin
Stars
DefinitionA limonoid found in Azadirachta indica.
Last Modified3 March 2015
DownloadsMolfile
FormulaC36H46O16
Net Charge0
Average Mass734.748
Monoisotopic Mass734.27859
SMILES[H][C@@]12OC=C[C@]1(O)[C@]1([H])C[C@H](O2)[C@@]2(O)[C@]1(C)O[C@]1([H])[C@]3([H])OC[C@]4(C(=O)OC)[C@H](OC(C)=O)C[C@H](OC(=O)/C(C)=C/C)[C@@]5(CO[C@](OC)(C(=O)OC)[C@@]5([H])[C@@]12C)[C@@]34[H]
InChIInChI=1S/C36H46O16/c1-9-16(2)25(38)50-19-13-20(49-17(3)37)33(27(39)43-6)14-47-22-23(33)32(19)15-48-35(45-8,28(40)44-7)26(32)30(4)24(22)52-31(5)18-12-21(36(30,31)42)51-29-34(18,41)10-11-46-29/h9-11,18-24,26,29,41-42H,12-15H2,1-8H3/b16-9+/t18-,19+,20-,21+,22-,23-,24-,26+,29+,30-,31-,32+,33+,34+,35+,36+/m1/s1
InChIKeyIRLZLBSKSFBHPL-JNIVOBJJSA-N
Species of MetaboliteComponentSourceComments
Azadirachta indica (ncbitaxon:124943) seed (BTO:0001226) PubMed (21381696) Defatted MeOH extract of seeds
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)
3-acetyl-11-methoxy-1-tigloylazadirachtinin (CHEBI:67303) has functional parent tiglic acid (CHEBI:9592)
3-acetyl-11-methoxy-1-tigloylazadirachtinin (CHEBI:67303) has role plant metabolite (CHEBI:76924)
3-acetyl-11-methoxy-1-tigloylazadirachtinin (CHEBI:67303) is a acetate ester (CHEBI:47622)
3-acetyl-11-methoxy-1-tigloylazadirachtinin (CHEBI:67303) is a ether (CHEBI:25698)
3-acetyl-11-methoxy-1-tigloylazadirachtinin (CHEBI:67303) is a limonoid (CHEBI:39434)
3-acetyl-11-methoxy-1-tigloylazadirachtinin (CHEBI:67303) is a methyl ester (CHEBI:25248)
IUPAC Name 
dimethyl (2aS,3R,5S,5aS,8S,8aR,8bS,8cR,9S,10aS,13aS,14S,14aR,15aS,15bR,15cR)-3-(acetyloxy)-8c,13a-dihydroxy-8-methoxy-8b,14a-dimethyl-5-{[(2E)-2-methylbut-2-enoyl]oxy}-4,5,8,8a,8b,8c,9,10a,13a,14,14a,15a,15b,15c-tetradecahydro-2H-9,14-methanodifuro[2'',3'',4'':4',5';4''',3''':1',8a']naphtho[2',3':4,5]furo[2,3-e]furo[2,3-b]oxepine-2a,8(3H)-dicarboxylate
Synonym  Source
1-O-tigloyl-3-acetyl-11-O-methylazadirachtininChEBI
Registry NumbersSources
Reaxys:5221283Reaxys
Citations