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Entry
CA00096                                                            

Classification
Carotenoid Name
Spirilloxanthin;
Rhodoviolascin
IUPAC name 1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-psi,psi-carotene
Formula
C42H60O2
Molecular Weight 
596.9 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Present in light harvesting complexes of photosynthetic bacteria Rhodospirillum ruburum (Ref.462).
  • Number of
    conjugated double bonds 
    13
    Number of
    conjugated multiple bonds 
    13
    Isomers 
  • Cis/trans isomer: CA00097
  • Constitutional isomer: CA00380, CA00622
  • InChI
    InChI=1S/C42H60O2/c1-35(23-15-25-37(3)27-17-29-39(5)31-19-33-41(7,8)43-11)21-13-14-22-36(2)24-16-26-38(4)28-18-30-40(6)32-20-34-42(9,10)44-12/h13-32H,33-34H2,1-12H3/b14-13+,23-15+,24-16+,27-17+,28-18+,31-19+,32-20+,35-21+,36-22+,37-25+,38-26+,39-29+,40-30+
    InChIKey
    VAZQBTJCYODOSV-HZUCFJANSA-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(/C=C/C=C(/C=C/CC(OC)(C)C)\C)\C)\C)/C)/C)/C)(C)C
    XLogP
    13.180
    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
    44
    TPSA
    (Topological Polar Surface Area) 
    18.460 Å2
    Source organisms
    Rhodospirillum rubrum (Ref.337) - Alphaproteobacteria: phototrophic purple bacteria
    Rhodobacter sphaeroides (Ref.343) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Rhodopesudomonnas palustris (Ref.344) - 
    Rubrivivax gelatinosus (Ref.546) - Betaproteobacteria: phototrophic purple nonsulfur bacteria
    Thiocapsa sp. (Ref.360) - purple sulfur bacteria
    Erythrobacter longus (Ref.364) - Alphaproteobacteria: marine anoxygenic phototroph with BChl a
    References
  • 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.343 : Niedzwiedzki, Dariusz M.; Dilbeck, Preston L.; Tang, Qun; Mothersole, David J.; Martin, Elizabeth C.; Bocian, David F.; Holten, Dewey; Hunter, C. Neil, Niedzwiedzki, Dariusz M.; Dilbeck, Preston L.; Tang, Qun; Mothersole, David J.; Martin, Elizabeth C.; Bocian, David F.; Holten, Dewey; Hunter, C. Neil, "Functional characteristics of spirilloxanthin and keto-bearing Analogues in light-harvesting LH2 complexes from Rhodobacter sphaeroides with a genetically modified carotenoid synthesis pathway".
  • Ref.344 : Zhao, Chun-gui; Fu, Qiao-ming; Zhuo, Min-quan; Yang, Su-ping, Weishengwuxue Tongbao (2014), 41(7), 1448-1455., "The relative polarity and stability of each carotenoid of spirilloxanthin biosynthesis pathway by thin-layer chromatography (TLC)".
  • Ref.546 : Sabine STEIGER, Chantal ASTIER and Gerhard SANDMANN, Biochem. J. (2000) 349, 635–640, "Substrate specificity of the expressed carotenoid 3,4-desaturase from Rubrivivax gelatinosus reveals the detailed reaction sequence to spheroidene and spirilloxanthin".
  • 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.364 : S. Takaichi, K. Shimada, and J. Ishidsu, Arch Microbiol.(1990) 153:118-122, "Carotenoids from the aerobic photosynthetic bacterium, Erythrobacter longus: β-Carotene and its hydroxyl derivatives".
  • 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
    34255-08-8
    Links to other DB
    KEGG COMPOUND: C15881
    KNApSAcK: C00022893
    LipidBank: VCA1040
    MassBank: CA000160
    ProCarDB: C1915

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