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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   
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
InChI=1S/C41H54O2/c1-31(19-14-21-33(3)23-16-24-36(6)40(42)29-30-41(9,10)43-11)17-12-13-18-32(2)20-15-22-34(4)25-27-39-28-26-35(5)37(7)38(39)8/h12-28H,29-30H2,1-11H3/b13-12+,19-14+,20-15+,23-16+,27-25+,31-17+,32-18+,33-21+,34-22+,36-24+
InChIKey
FSQZIFSGNDUYRQ-TYKRLFMMSA-N
Canonical SMILES
COC(CCC(=O)/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/c1ccc(c(c1C)C)C)\C)\C)/C)/C)/C)(C)C
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
Source organisms
Thiocapsa sp. (Ref.360) - purple sulfur bacteria
Lamprocystis roseopersicina (Ref.121) - purple sulfur bacteria
Thiodictyon sp. (Ref.439) - purple sulfur bacteria
Thiothece gelatinosa (Ref.351) - purple sulfur bacteria
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".
  • CAS
    16840-70-3
    Links to other DB
    KEGG COMPOUND: C16280
    KNApSAcK: C00022998
    LipidBank: VCA1170
    ProCarDB: C1845

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