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Entry
CA00717                                                            
Classification
Carotenoid Name
Okenone
IUPAC name 1'-Methoxy-1',2'-dihydro-chi,psi-caroten-4'-one
Formula
C41H54O2
Molecular Weight 
578.842 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
14 including one ketone (14 in total)
Number of
conjugated multiple bonds 
14 including one ketone (14 in total)
Isomers 
InChI

InChIKey

Canonical SMILES

XLogP
14.005
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
2
Complexity of molecule
0.062
Number of heavy atoms
43
TPSA
(Topological Polar Surface Area) 
26.300 Å2
Reaction
  • Product: CR00152
    • Pathway
  • Pathway: CB000054
    • Major carotenoid information
    Major carotenoid in purple sulfur bacterium Thiocapsa marina (Ref.718). Predominant carotenoid in purple-violet Thiocapsa strain 5811 (Ref.717).
    Minor carotenoid information

    Source organisms
    Thiodictyon sp. (Ref.439) - purple sulfur bacteria (Gammaproteobacteria - Chromatiaceae)
    Lamprocystis roseopersicina (Ref.121) - purple sulfur bacteria (Gammaproteobacteria - Chromatiaceae)
    Thiocystis gelatinosa (Ref.351) - purple sulfur bacteria, same as Thiothece gelatinosa (Gammaproteobacteria - Chromatiaceae)
    Thiocapsa sp. (Ref.360) - purple sulfur bacteria (Gammaproteobacteria - Chromatiaceae)
    References
  • Ref.360: Pierre Caumette, Karin Schmidt, Hanno Biebl, Norbert Pfennig, Systematic and Applied Microbiology, Volume 6, Issue 2, September 1985, Pages 132–136, "Characterization of a Thiocapsa Strain Containing Okenone as Major Carotenoid".
  • Ref.121: Pfennig, Norbert; Markham, M. Clare; Liaaen-Jensen, Synnoeve, Archiv fuer Mikrobiologie (1968), 62, 178-91., "Carotenoids of Thiorhodaceae. VIII. Isolation and characterization of a Thiothece, Lamprocystis, and Thiodictyon strain and their carotenoid pigments".
  • Ref.439: Kajetan Vogl, and Donald A. Bryant, "Elucidation of the Biosynthetic Pathway for Okenone in Thiodictyon sp. CAD16 Leads to the Discovery of Two Novel Carotene Ketolases".
  • Ref.351: Francis, G. W.; Liaaen Jensen, Synnoeve, Acta Chemica Scandinavica (1947-1973) (1970), 24(8), 2705-12., "Bacterial carotenoids. XXXIII. Carotenoids of thiorhodaceae. 9. Structures of the carotenoids of the rhodopinal series".
  • Ref.718: Pierre Caumette, Remy Guyoneaud, Johannes F. Imhoff, Jorg Suiing and Vladimir Gorlenko, International Journal of Systematic and Evolutionary Microbiology (2004), 54, 1031–1036, "Thiocapsa marina sp. nov., a novel, okenonecontaining purple sulfur bacterium isolated from brackish coastal and marine environments".
  • Ref.717: Pierre Caumette, Karin Schmidt, Hanno Biebl, and Norbert Pfennig, Systematic and Applied Microbiology Volume 6, Issue 2, September 1985, Pages 132-136, "Characterization of a Thiocapsa Strain Containing Okenone as Major Carotenoid", https://doi.org/10.1016/S0723-2020(85)80045-X.
    • CAS
    16840-70-3
    Links to other DB
    KEGG COMPOUND: C16280
    KNApSAcK: C00022998
    LipidBank: VCA1170
    ProCarDB: C1845

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