Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00081   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00081                                                            

Classification
Carotenoid Name
Spheroidene
IUPAC name 1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-psi,psi-carotene
Formula
C41H60O
Molecular Weight 
568.89 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10
Number of
conjugated multiple bonds 
10
Isomers 
  • Cis/trans isomer: CA00082
  • Constitutional isomer: CA00133
  • InChI
    InChI=1S/C41H60O/c1-34(2)20-14-23-37(5)26-17-29-38(6)27-15-24-35(3)21-12-13-22-36(4)25-16-28-39(7)30-18-31-40(8)32-19-33-41(9,10)42-11/h12-13,15-16,18-22,24-28,30-32H,14,17,23,29,33H2,1-11H3/b13-12+,24-15+,25-16+,30-18+,32-19+,35-21+,36-22+,37-26+,38-27+,39-28+,40-31+
    InChIKey
    FJOCMTHZSURUFA-AXYGSFPTSA-N
    Canonical SMILES
    COC(C/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
    13.925
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    9.230 Å2
    Source organisms
    Rhodospirillum rubrum (Ref.207, Ref.337) - Alphaproteobacteria: phototrophic purple bacteria
    Rubrivivax gelatinosus (Ref.354) - Betaproteobacteria: phototrophic purple nonsulfur bacteria
    Rhodobacter sphaeroides (Ref.208) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    References
  • Ref.207 : B. H. Davies, E. Ann Holmes, D. E. Loeber, T. P. Toube, and B. C. L. Weedon, J. Chem. Soc. C, 1969, 1266-1268, DOI: 10.1039/J39690001266, "Carotenoids and related compounds. Part XXIII. Occurrence of 7,8,11,12-tetrahydrolycopene, spheroidene, 3,4,11′,12′-tetrahydrospheroidene, and 11′,12′-dihydrospheroidene in Rhodospirillum rubrum".
  • Ref.337 : H.C. Malhotra, G. Britton, T.W. Goodwin, Phytochemistry, Volume 9, Issue 11, November 1970, Pages 2369–2375, "The mono- and dimethoxy-carotenoids of diphenylamine-inhibited cultures of rhodospirillum rubrum".
  • 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.208 : M Albrecht, A Ruther, G Sandmann, J. Bacteriol. December 1997 vol. 179 no. 23 7462-7467, "Purification and biochemical characterization of a hydroxyneurosporene desaturase involved in the biosynthetic pathway of the carotenoid spheroidene in Rhodobacter sphaeroides.".
  • CAS
    13836-61-8
    Links to other DB
    KEGG COMPOUND: C15900
    LipidBank: VCA1037
    ProCarDB: C1930

       Search other references with Google Scholar