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Entry
CA00157                                                            

Classification
Carotenoid Name
Rhodobacterioxanthin
IUPAC name (13Z)-1,1'-Dimethoxy-3,4,3',4'-tetradehydro-1,2,1',2'-tetrahydro-psi,psi-caroten-20-al
Formula
C42H58O3
Molecular Weight 
610.884 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Antioxidant activity - lipid peroxidation inhibitor nearly equal to that of Lycopene (Ref.352).
  • Naturally occuring purple color (Ref.352).
  • Number of
    conjugated double bonds 
    12 including one aldehyde (12 in total)
    Number of
    conjugated multiple bonds 
    12 including one aldehyde (12 in total)
    Isomers 
    InChI
    InChI=1S/C41H58O3/c1-34(20-14-21-35(2)23-16-25-38(5)30-32-41(8,9)44-11)19-12-13-28-39(33-42)29-17-26-36(3)22-15-24-37(4)27-18-31-40(6,7)43-10/h12-29,33H,30-32H2,1-11H3/b13-12+,20-14+,22-15+,23-16+,27-18+,29-17+,34-19+,35-21+,36-26+,37-24+,38-25+,39-28+
    InChIKey
    NLSHXTJPFWTWFP-REIHPGBOSA-N
    Canonical SMILES
    O=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(/CCC(OC)(C)C)\C)\C)\C)/C=C/C=C(/C=C/C=C(/C=C/CC(OC)(C)C)\C)\C
    XLogP
    11.314
    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
    44
    TPSA
    (Topological Polar Surface Area) 
    35.530 Å2
    Source organisms
    Rhodobacter capsulatus (Ref.352) - Alphaproteobacteria: photosynthetic purple nonsulfur bacterium
    References
  • Ref.352 : Maoka, Takashi; Mochida, Kooichi; Okuda, Yoko; Ito, Yoshihiro; Fujiwara, Yasuhiro, Chemical & Pharmaceutical Bulletin¬†(1997),¬†45(7),¬†1225-1227., "A novel purple carotenoid, rhodobacterioxanthin, from Rhodobacter capsulatus".
  • CAS
    183308-55-6
    Links to other DB
    KNApSAcK: C00022964
    LipidBank: VCA1171

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