CHEBI:59685 - edaxadiene

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name edaxadiene
Definition A bicyclic halimane-type diterpenoid produced by the pathogen Mycobacterium tuberculosis as a defense against macrophage attack. The structure was revised in 2010, having been initially thought to be tricyclic. The compound was originally named nosyberkol after it was first isolated in 2004 from a sponge, Raspailia sp., collected from the Nosy Be island of Madagascar.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C20H34O
Net Charge 0
Average Mass 290.48340
Monoisotopic Mass 290.261
InChI InChI=1S/C20H34O/c1-7-19(5,21)13-14-20(6)15(2)10-11-16-17(20)9-8-12-18(16,3)4/h7,11,15,17,21H,1,8-10,12-14H2,2-6H3/t15-,17+,19?,20+/m0/s1
SMILES [H][C@@]12CCCC(C)(C)C1=CC[C@H](C)[C@@]2(C)CCC(C)(O)C=C
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing edaxadiene (CHEBI:59685) has role metabolite (CHEBI:25212)
edaxadiene (CHEBI:59685) is a carbobicyclic compound (CHEBI:36785)
edaxadiene (CHEBI:59685) is a halimane diterpenoid (CHEBI:59686)
edaxadiene (CHEBI:59685) is a tertiary alcohol (CHEBI:26878)
Incoming (13R)-edaxadiene (CHEBI:63178) is a edaxadiene (CHEBI:59685)
(13S)-edaxadiene (CHEBI:63180) is a edaxadiene (CHEBI:59685)
Synonyms Sources
isotuberculosinol ChEBI
nosyberkol ChEBI
Registry Number Type Source
20769504 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15568794 PubMed citation Europe PMC
19583202 PubMed citation Europe PMC
20462237 PubMed citation Europe PMC
21228491 PubMed citation Europe PMC
21290071 PubMed citation Europe PMC
Last Modified
15 November 2011
General Comment
2011-11-15 For a correction to the paper by Mann FM, Xu M, Chen X, Fulton DB, Russell DG and Peters RJ (2009) Edaxadiene: a new bioactive diterpene from Mycobacterium tuberculosis. J. Am. Chem. Soc., 2009, 131, 17526-7 [MED:19583202], see J. Am. Chem. Soc., 2010, 132(31), 10953.