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CHEBI:67297 - 7-deacetyl-7-benzoylgedunin

ChEBI IDCHEBI:67297
ChEBI Name7-deacetyl-7-benzoylgedunin
Stars
DefinitionA limonoid that is gedunin in which the acetoxy group at position 7 is replaced by a benzoyloxy group. Isolated from Azadirachta indica, it exhibits cytotoxic activity against HL60 leukemia cells.
Last Modified9 January 2014
DownloadsMolfile
FormulaC33H36O7
Net Charge0
Average Mass544.644
Monoisotopic Mass544.24610
SMILES[H][C@]12CC[C@@]3(C)[C@H](c4ccoc4)OC(=O)[C@@]4([H])O[C@@]34[C@]1(C)[C@H](OC(=O)c1ccccc1)C[C@@]1([H])C(C)(C)C(=O)C=C[C@]21C
InChIInChI=1S/C33H36O7/c1-29(2)22-17-24(38-27(35)19-9-7-6-8-10-19)32(5)21(30(22,3)14-12-23(29)34)11-15-31(4)25(20-13-16-37-18-20)39-28(36)26-33(31,32)40-26/h6-10,12-14,16,18,21-22,24-26H,11,15,17H2,1-5H3/t21-,22+,24-,25+,26-,30-,31+,32+,33-/m1/s1
InChIKeyFJGQKVDLYYRRKR-VHSMAHMUSA-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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) has functional parent gedunin (CHEBI:65954)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) has role antineoplastic agent (CHEBI:35610)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) has role plant metabolite (CHEBI:76924)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a benzoate ester (CHEBI:36054)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a cyclic terpene ketone (CHEBI:36130)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a enone (CHEBI:51689)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a epoxide (CHEBI:32955)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a furans (CHEBI:24129)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a limonoid (CHEBI:39434)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a pentacyclic triterpenoid (CHEBI:25872)
7-deacetyl-7-benzoylgedunin (CHEBI:67297) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4aR,6R,6aS,6bR,7aS,10R,10aS,12aR,12bR)-10-(furan-3-yl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydronaphtho[2,1-f]oxireno[d]isochromen-6-yl benzoate
Registry NumbersSources
Reaxys:6552768Reaxys
Citations