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edaxadiene (CHEBI:59685)

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ChEBI Name edaxadiene
ChEBI ID CHEBI:59685
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
See structure as:  Image  Applet
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Formula Source
C20H34O ChEBI
Net Charge 0
Average Mass 290.48340
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
InChIKey
TXBORCBWDUAHAC-AIQOQHTRSA-N
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 on the 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)
IUPAC Name
3-methyl-5-[(1R,2S,8aS)-1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]pent-1-en-3-ol
Synonyms Sources
isotuberculosinol ChEBI
nosyberkol ChEBI
Registry Number Type Source
20769504 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15568794 PubMed citation CiteXplore
19583202 PubMed citation CiteXplore
20462237 PubMed citation CiteXplore
21228491 PubMed citation CiteXplore
21290071 PubMed citation CiteXplore
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.
 
Last Modified
15 November 2011

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