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Entry
CA00174                                                            

Classification
Carotenoid Name
2-Ketospirilloxanthin;
2-Oxospirilloxanthin
IUPAC name 1,1'-Dimethoxy-3,4,3',4'-tetrahydro-1,2,1',2'-tetrahydro-psi,psi-caroten-2-one
Formula
C42H58O3
Molecular Weight 
610.884 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 
  • Constitutional isomer: CA00947
  • InChI
    InChI=1S/C42H58O3/c1-34(22-15-24-36(3)26-17-28-38(5)30-19-33-41(7,8)44-11)20-13-14-21-35(2)23-16-25-37(4)27-18-29-39(6)31-32-40(43)42(9,10)45-12/h13-32H,33H2,1-12H3/b14-13+,22-15+,23-16+,26-17+,27-18+,30-19+,32-31+,34-20+,35-21+,36-24+,37-25+,38-28+,39-29+
    InChIKey
    AUIMFBMJZYMMRO-MRLRKSOKSA-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/C(=O)C(OC)(C)C)\C)\C)\C)/C)/C)/C)(C)C
    XLogP
    11.891
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    35.530 Å2
    Source organisms
    Rhodopseudomonas spheroides (Ref.342, Ref.343) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Rhodopseudomonas gelatinosa (Ref.342) - Betaproteobacteria: purple nonsulfur bacteria
    References
  • Ref.342 : Jackman, L. M.; Jensen, S. Liaaen, Acta Chemica Scandinavica (1403-1411)(1964), Pages: 1403-1411, "Bacterial Carotenoids. XV. On the Constitution of the Minor Carotenoids of Rhodopseudomonas. 5. The Structures of P518 (2,2'-Diketo-spirilloxanthin), OH-R (OH-Spheroidenone), and OH-Y (OH-Spheroidene).".
  • 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".
  • CAS
    106423-77-2
    Links to other DB
    KEGG COMPOUND: C15884
    KNApSAcK: C00023013
    LipidBank: VCA1071
    ProCarDB: C0400

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