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Entry
CA00165                                                            

Classification
Carotenoid Name
Spheroidenone
IUPAC name 1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-psi,psi-caroten-2-one
Formula
C41H58O2
Molecular Weight 
582.874 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Present in light harvesting complexes of photosynthetic bacteria Rhodopseudomonas capsulata, and Rhodopseudomonas spheroides (Ref.462).
  • Number of
    conjugated double bonds 
    11 including one ketone (11 in total)
    Number of
    conjugated multiple bonds 
    11 including one ketone (11 in total)
    Isomers 
  • Constitutional isomer: CA00090, CA00156, CA00166, CA00265, CA00376
  • InChI
    InChI=1S/C41H58O2/c1-33(2)19-14-22-36(5)25-17-28-37(6)26-15-23-34(3)20-12-13-21-35(4)24-16-27-38(7)29-18-30-39(8)31-32-40(42)41(9,10)43-11/h12-13,15-16,18-21,23-27,29-32H,14,17,22,28H2,1-11H3/b13-12+,23-15+,24-16+,29-18+,32-31+,34-20+,35-21+,36-25+,37-26+,38-27+,39-30+
    InChIKey
    ZQFURSYWJPLAJR-FZFXUSNISA-N
    Canonical SMILES
    COC(C(=O)/C=C/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C)/C)/C)/C)(C)C
    XLogP
    12.636
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    26.300 Å2
    Source organisms
    Gelliodes callista (Ref.253) - Sea sponge
    Rhodobaca bogoriensis (Ref.339) - Alphaproteobacteria: alkaliphilic purple non-sulfur bacteria from African Rift Valley soda lakes
    Rubrivivax gelatinosus (Ref.354) - Betaproteobacteria: phototrophic purple nonsulfur bacteria
    Roseobacter denitrificans (Ref.361) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    References
  • Ref.253 : Tanaka, Yoshito; Inoue, Tsuyoshi, Nippon Suisan Gakkaishi (1987), 53(7), 1271-3., "new aldehydic carotenoid gelliodesxanthin from sea sponge Gelliodes callista".
  • Ref.339 : Takaichi, Shinichi; Jung, Deborah O.; Madigan, Michael T., Photosynthesis Research (2001), 67(3), 207-214., "Accumulation of unusual carotenoids in the spheroidene pathway, demethylspheroidene and demethylspheroidenone, in an alkaliphilic purple nonsulfur bacterium Rhodobaca bogoriensis".
  • Ref.354 : Jirsakova, Vladimira; Reiss-Husson, Francoise; van Dijk, Bas; Owen, Gabrielle; Hoff, Arnold J., Photochemistry and Photobiology (1996), 64(2), 363-368., "Characterization of carotenoid triplet states in the light-harvesting complex B800-850 from the purple bacterium Rubrivivax gelatinosus".
  • Ref.361 : Shinichi Takaichi, Kazuo Furihata, Keiji Harashima, Archives of Microbiology, April 1991, Volume 155, Issue 5, pp 473-476, "Light-induced changes of carotenoid pigments in anaerobic cells of the aerobic photosynthetic bacterium, Roseobacter denitrificans (Erythrobacter species OCh 114): reduction of spheroidenone to 3,4-dihydrospheroidenone" .
  • Ref.462 : GERHART DREWS, MICROBIOLOGICAL REVIEWS, Mar. 1985, p. 59-70 , "Structure and Functional Organization of Light-Harvesting Complexes and Photochemical Reaction Centers in Membranes of Phototrophic Bacteria".
  • CAS
    13836-70-9
    Links to other DB
    KEGG COMPOUND: C15903
    KNApSAcK: C00000914
    LipidBank: VCA1039
    MassBank: CA000102
    ProCarDB: C1940

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