CHEBI:67290 - azadiradionolide

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ChEBI Name azadiradionolide
ChEBI ID CHEBI:67290
Definition A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by a oxo groups at positions 3 and 16, an acetoxy group at position 7 and a 2-oxo-2,5-dihydrofuran-3-yl group at position 17. It has been isolated from Azadirachta indica.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H34O6
Net Charge 0
Average Mass 466.56600
Monoisotopic Mass 466.23554
InChI InChI=1S/C28H34O6/c1-15(29)34-22-14-19-25(2,3)21(31)8-11-26(19,4)18-7-10-27(5)20(28(18,22)6)13-17(30)23(27)16-9-12-33-24(16)32/h8-9,11,13,18-19,22-23H,7,10,12,14H2,1-6H3/t18-,19+,22-,23-,26-,27+,28-/m1/s1
InChIKey ANQXYDNAHFDKKH-AFEVRESMSA-N
SMILES CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@]3(C)[C@@H](C(=O)C=C3[C@]12C)C1=CCOC1=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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing azadiradionolide (CHEBI:67290) has role metabolite (CHEBI:25212)
azadiradionolide (CHEBI:67290) has role plant metabolite (CHEBI:76924)
azadiradionolide (CHEBI:67290) is a acetate ester (CHEBI:47622)
azadiradionolide (CHEBI:67290) is a butenolide (CHEBI:50523)
azadiradionolide (CHEBI:67290) is a cyclic terpene ketone (CHEBI:36130)
azadiradionolide (CHEBI:67290) is a limonoid (CHEBI:39434)
azadiradionolide (CHEBI:67290) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name
(5α,7α,17α)-4,4,8-trimethyl-3,16-dioxo-17-(2-oxo-2,5-dihydrofuran-3-yl)androsta-1,14-dien-7-yl acetate
Synonym Source
24,25,26,27-tetranorapoeupha-7α-acetoxy-21,23-epoxy-1,14,20(22)-trien-3,16,21-trione ChEBI
Registry Number Type Source
8368313 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10425127 PubMed citation Europe PMC
21381696 PubMed citation Europe PMC
Last Modified
18 November 2013