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CHEBI:67290 - azadiradionolide

Default Structure
ChEBI IDCHEBI:67290
ChEBI Nameazadiradionolide
Stars
DefinitionA 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.
Last Modified18 November 2013
DownloadsMolfile
FormulaC28H34O6
Net Charge0
Average Mass466.574
Monoisotopic Mass466.23554
SMILES[H][C@@]1(C2=CCOC2=O)C(=O)C=C2[C@]1(C)CC[C@]1([H])[C@@]3(C)C=CC(=O)C(C)(C)[C@]3([H])C[C@@H](OC(C)=O)[C@@]21C
InChIInChI=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
InChIKeyANQXYDNAHFDKKH-AFEVRESMSA-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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
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-trioneChEBI
Registry NumbersSources
Reaxys:8368313Reaxys
Citations