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CHEBI:76293 - azadirone

ChEBI IDCHEBI:76293
ChEBI Nameazadirone
Stars
DefinitionA tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by an oxo group at position 3, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antiplasmodial and antineoplastic activities.
Last Modified30 May 2024
Submitternamrata
DownloadsMolfile
FormulaC28H36O4
Net Charge0
Average Mass436.592
Monoisotopic Mass436.26136
SMILES[H][C@]12CC[C@]3(C)C(=CC[C@@]3([H])c3ccoc3)[C@]1(C)[C@H](OC(C)=O)C[C@@]1([H])C(C)(C)C(=O)C=C[C@]21C
InChIInChI=1S/C28H36O4/c1-17(29)32-24-15-22-25(2,3)23(30)10-13-27(22,5)21-9-12-26(4)19(18-11-14-31-16-18)7-8-20(26)28(21,24)6/h8,10-11,13-14,16,19,21-22,24H,7,9,12,15H2,1-6H3/t19-,21+,22-,24+,26-,27+,28-/m0/s1
InChIKeyXXIKKMLIDXLAIK-RFKFVWFBSA-N
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.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
ChEBI Ontology
Outgoing Relation(s)
azadirone (CHEBI:76293) has role antineoplastic agent (CHEBI:35610)
azadirone (CHEBI:76293) has role antiplasmodial drug (CHEBI:64915)
azadirone (CHEBI:76293) has role plant metabolite (CHEBI:76924)
azadirone (CHEBI:76293) is a acetate ester (CHEBI:47622)
azadirone (CHEBI:76293) is a cyclic terpene ketone (CHEBI:36130)
azadirone (CHEBI:76293) is a furans (CHEBI:24129)
azadirone (CHEBI:76293) is a limonoid (CHEBI:39434)
azadirone (CHEBI:76293) is a tetracyclic triterpenoid (CHEBI:26893)
Incoming Relation(s)
20,21,22,23-tetrahydro-23-oxoazadirone (CHEBI:67291) has functional parent azadirone (CHEBI:76293)
IUPAC Name 
(5α,7α,13α,17α)-17-(furan-3-yl)-4,4,8-trimethyl-3-oxoandrosta-1,14-dien-7-yl acetate
UniProt Name  Source
azadironeUniProt
Registry NumbersSources
Reaxys:4214438Reaxys
CAS:25279-67-8ChemIDplus
Citations