CHEBI:67280 - azadiradione

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ChEBI Name azadiradione
ChEBI ID CHEBI:67280
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C28H34O5
Net Charge 0
Average Mass 450.56660
Monoisotopic Mass 450.24062
InChI InChI=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
InChIKey KWAMDQVQFVBEAU-HMWIRDDCSA-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)c1ccoc1
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): 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.
Application(s): 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.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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-,acetate ChemIDplus
Registry Numbers Types Sources
26241-51-0 CAS Registry Number ChemIDplus
5858436 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12713364 PubMed citation Europe PMC
1593280 PubMed citation Europe PMC
18617378 PubMed citation Europe PMC
19475987 PubMed citation Europe PMC
22928548 PubMed citation Europe PMC
Last Modified
09 January 2014