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CHEBI:67280 - azadiradione

ChEBI IDCHEBI:67280
ChEBI Nameazadiradione
Stars
DefinitionA tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by oxo groups at positions 3 and 16, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antimycobacterial and anti-inflammatory activities.
Last Modified9 January 2014
DownloadsMolfile
FormulaC28H34O5
Net Charge0
Average Mass450.575
Monoisotopic Mass450.24062
SMILES[H][C@]12CC[C@]3(C)C(=CC(=O)[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/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,14H2,1-6H3/t19-,20+,23-,24-,26-,27-,28-/m1/s1
InChIKeyKWAMDQVQFVBEAU-HMWIRDDCSA-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.
antimycobacterial drug  A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antimycobacterial drug  A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.
ChEBI Ontology
Outgoing Relation(s)
azadiradione (CHEBI:67280) has role anti-inflammatory agent (CHEBI:67079)
azadiradione (CHEBI:67280) has role antimycobacterial drug (CHEBI:64912)
azadiradione (CHEBI:67280) has role plant metabolite (CHEBI:76924)
azadiradione (CHEBI:67280) is a acetate ester (CHEBI:47622)
azadiradione (CHEBI:67280) is a cyclic terpene ketone (CHEBI:36130)
azadiradione (CHEBI:67280) is a furans (CHEBI:24129)
azadiradione (CHEBI:67280) is a limonoid (CHEBI:39434)
azadiradione (CHEBI:67280) is a tetracyclic triterpenoid (CHEBI:26893)
Incoming Relation(s)
15-hydroxyazadiradione (CHEBI:67283) has functional parent azadiradione (CHEBI:67280)
17-hydroxyazadiradione (CHEBI:67284) has functional parent azadiradione (CHEBI:67280)
desfuranoazadiradione (CHEBI:67292) has functional parent azadiradione (CHEBI:67280)
epoxyazadiradione (CHEBI:67285) has functional parent azadiradione (CHEBI:67280)
IUPAC Name 
(5α,7α,13α,17α)-17-(furan-3-yl)-4,4,8-trimethyl-3,16-dioxoandrosta-1,14-dien-7-yl acetate
Synonym  Source
24-Nor-5alpha,13alpha,17alpha-chola-1,14,20,22-tetraene-3,16-dione, 21,23-epoxy-7alpha-hydroxy-4,4,8-trimethyl-,acetateChemIDplus
Registry NumbersSources
Reaxys:5858436Reaxys
CAS:26241-51-0ChemIDplus
Citations