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Carotenoids DB          Carotenoids DB: CA00165   
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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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00349
  • Product: CR00249
    • Pathway
  • Pathway: CB000022,  CB000048
    • Major carotenoid information
    Major carotenoid in Rhodobacter sphaeroides (Ref.740).
    Minor carotenoid information

    Source organisms
    Rubrivivax gelatinosus (Ref.354) - Betaproteobacteria: phototrophic purple nonsulfur bacteria (Betaproteobacteria - Unclassified Burkholderiales)
    Roseobacter denitrificans (Ref.361) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria (Alphaproteobacteria - Rhodobacteraceae)
    Rhodobaca bogoriensis (Ref.339) - Alphaproteobacteria: alkaliphilic purple non-sulfur bacteria from African Rift Valley soda lakes (Alphaproteobacteria - Rhodobacteraceae)
    Gelliodes callista (Ref.253) - Sea sponge (Porifera - Niphatiidae)
    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".
  • Ref.740: Chih-Chiang Wang el al., Food & Nutrition Research 2016, 60: 29580 - "Extract from a mutant Rhodobacter sphaeroides as an enriched carotenoid source", http://dx.doi.org/10.3402/fnr.v60.29580.
    • CAS
    13836-70-9
    Links to other DB
    KEGG COMPOUND: C15903
    KNApSAcK: C00000914
    LipidBank: VCA1039
    MassBank: CA000102
    ProCarDB: C1940

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