CHEBI:67297 - 7-deacetyl-7-benzoylgedunin

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ChEBI Name 7-deacetyl-7-benzoylgedunin
ChEBI ID CHEBI:67297
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C33H36O7
Net Charge 0
Average Mass 544.63470
Monoisotopic Mass 544.24610
InChI InChI=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
InChIKey FJGQKVDLYYRRKR-VHSMAHMUSA-N
SMILES CC1(C)[C@@H]2C[C@@H](OC(=O)c3ccccc3)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)c3ccoc3)[C@@]2(C)C=CC1=O
Metabolite of Species Details
Azadirachta indica (NCBI:txid124943) Found in seed (BTO:0001226). Defatted MeOH extract of seeds See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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)
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 Number Type Source
6552768 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21381696 PubMed citation Europe PMC
Last Modified
09 January 2014