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Entry
CA00073                                                            

Classification
Carotenoid Name
Rhodopin;
1-Hydroxylycopene;
1-Hydroxy-1,2-dihydrolycopene;
1-Hydroxy-lycopene
IUPAC name 1,2-Dihydro-psi,psi-caroten-1-ol
Formula
C40H58O
Molecular Weight 
554.864 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11
Number of
conjugated multiple bonds 
11
Isomers 
  • Constitutional isomer: CA00074, CA00202, CA00201
  • InChI
    InChI=1S/C40H58O/c1-33(2)19-13-22-36(5)25-16-28-37(6)26-14-23-34(3)20-11-12-21-35(4)24-15-27-38(7)29-17-30-39(8)31-18-32-40(9,10)41/h11-12,14-17,19-21,23-30,41H,13,18,22,31-32H2,1-10H3/b12-11+,23-14+,24-15+,28-16+,29-17+,34-20+,35-21+,36-25+,37-26+,38-27+,39-30+
    InChIKey
    CNYVJTJLUKKCGM-RGGGOQHISA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(\CCC=C(C)C)/C)/C)/C)/C=C/C=C(/C=C/C=C(/CCCC(O)(C)C)\C)\C
    XLogP
    13.478
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    41
    TPSA
    (Topological Polar Surface Area) 
    20.230 Å2
    Source organisms
    Rhodopseudomonas palustris (Ref.336, Ref.344) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Rhodobacter sphaeroides (Ref.208) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Rhodobacter capsulatus (Ref.353) - Alphaproteobacteria: photosynthetic purple nonsulfur bacterium
    Phaeospirillum sp. (Ref.327) - Alphaproteobacteria: spiral-shaped phototrophic purple non-sulfur bacteria
    Roseospira sp. (Ref.327) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Thiodictyon strain 3011 (Ref.351) - purple sulfur bacteria
    References
  • Ref.336 : Zhang, Tong; Zhu, Rui-yan; Hui, Bo-di; Yang, Bo-yuan, Shipin Kexue (Beijing, China) (2013), 34(21), 283-291., "Lycopene biosynthesis in Rhodopseudomonas palustris".
  • 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.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.".
  • Ref.353 : Maoka, Takashi; Matsumura, Akihiko; Ito, Yoshihiro; Okuda, Yoko; Mochida, Koichi, Jpn. Kokai Tokkyo Koho (1996), JP 08239658 A 19960917., "Antioxidants of Rhodobacter".
  • Ref.327 : Takaichi, Shinichi; Maoka, Takashi; Sasikala, Ch.; Ramana, Ch. V.; Shimada, Keizo, Current Microbiology (2011), 63(1), 75-80., "Genus specific unusual carotenoids in purple bacteria, Phaeospirillum and Roseospira: Structures and biosyntheses".
  • Ref.351 : Francis, G. W.; Liaaen Jensen, Synnoeve, Acta Chemica Scandinavica (1947-1973) (1970), 24(8), 2705-12., "Bacterial carotenoids.  XXXIII.  Carotenoids of thiorhodaceae.  9.  Structures of the carotenoids of the rhodopinal series".
  • CAS
    105-92-0
    Links to other DB
    KEGG COMPOUND: C19795
    KNApSAcK: C00022854
    LipidBank: VCA1032
    MassBank: CA000159
    ProCarDB: C1904

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