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CHEBI:67305 - 6-deacetylnimbin

ChEBI IDCHEBI:67305
ChEBI Name6-deacetylnimbin
Stars
DefinitionA limonoid that is nimbin in which the acetyloxy group at position 6 is replaced by a hydroxy hroup. It has been isolated from Azadirachta indica.
Last Modified3 March 2015
DownloadsMolfile
FormulaC28H34O8
Net Charge0
Average Mass498.572
Monoisotopic Mass498.22537
SMILES[H][C@@]12[C@@H](O)[C@@]3([H])O[C@]4([H])C[C@@H](c5ccoc5)C(C)=C4[C@@]3(C)[C@H](CC(=O)OC)[C@@]1(C)C(=O)C=C[C@@]2(C)C(=O)OC
InChIInChI=1S/C28H34O8/c1-14-16(15-8-10-35-13-15)11-17-21(14)28(4)18(12-20(30)33-5)27(3)19(29)7-9-26(2,25(32)34-6)23(27)22(31)24(28)36-17/h7-10,13,16-18,22-24,31H,11-12H2,1-6H3/t16-,17-,18-,22-,23+,24-,26-,27+,28-/m1/s1
InChIKeyCTBHKOAPXBDFPX-PQYHCQQJSA-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.
insect growth regulator  A growth regulator that inhibits the life cycle of an insect.
Applications:
antifeedant  A substance that prevents pests from feeding.
insect growth regulator  A growth regulator that inhibits the life cycle of an insect.
ChEBI Ontology
Outgoing Relation(s)
6-deacetylnimbin (CHEBI:67305) has functional parent nimbin (CHEBI:67304)
6-deacetylnimbin (CHEBI:67305) has role antifeedant (CHEBI:22583)
6-deacetylnimbin (CHEBI:67305) has role insect growth regulator (CHEBI:24851)
6-deacetylnimbin (CHEBI:67305) has role plant metabolite (CHEBI:76924)
6-deacetylnimbin (CHEBI:67305) is a cyclic terpene ketone (CHEBI:36130)
6-deacetylnimbin (CHEBI:67305) is a diester (CHEBI:51307)
6-deacetylnimbin (CHEBI:67305) is a enone (CHEBI:51689)
6-deacetylnimbin (CHEBI:67305) is a furans (CHEBI:24129)
6-deacetylnimbin (CHEBI:67305) is a limonoid (CHEBI:39434)
6-deacetylnimbin (CHEBI:67305) is a methyl ester (CHEBI:25248)
6-deacetylnimbin (CHEBI:67305) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name 
methyl (2R,3aR,4aS,5R,5aR,6R,9aR,10S,10aR)-2-(furan-3-yl)-5-hydroxy-10-(2-methoxy-2-oxoethyl)-1,6,9a,10a-tetramethyl-9-oxo-3,3a,4a,5,5a,6,9,9a,10,10a-decahydro-2H-cyclopenta[b]naphtho[2,3-d]furan-6-carboxylate
Synonym  Source
nimbic acid dimethyl esterChemIDplus
Registry NumbersSources
Reaxys:70922Reaxys
CAS:18609-16-0ChemIDplus
Citations