EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:67290 - azadiradionolide

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:
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.
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