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Entry
CA01084                                                            

Classification
Carotenoid Name
Dinochrome B
IUPAC name (3S,5R,6R,3'S,5'R,8'S)-5',8'-epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-β,β-carotene-3,5,3'-triol 3-O-acetate
Formula
C44H60O5
Molecular Weight 
668.92 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - more effective than peridinin (Ref.494), significant growth-inhibitory activity toward cancer cells (Ref.569)
  • Antiproliferative activity on HeLa cells at the concentration of 25 g.mL-1 (Ref.494).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
  • Conformer: CA01083
  • InChI
    InChI=1S/C44H60O5/c1-31(21-16-22-32(2)20-14-15-25-39-42(8,9)29-37(48-35(5)45)30-43(39,10)47)18-12-13-19-33(3)23-17-24-34(4)38-26-40-41(6,7)27-36(46)28-44(40,11)49-38/h12-24,26,36-38,46-47H,27-30H2,1-11H3/b13-12+,20-14+,21-16+,23-17+,31-18+,32-22+,33-19+,34-24+/t25-,36-,37-,38-,43+,44+/m0/s1
    InChIKey
    DYTLPXMYTFXUBJ-ZPHPPGIZSA-N
    Canonical SMILES
    CC(=O)O[C@H]1CC(C)(C)C(=C=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/[C@@H]2C=C3[C@@](O2)(C)C[C@H](CC3(C)C)O)\C)\C)/C)/C)[C@](C1)(C)O
    XLogP
    10.499
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    2
    Complexity of molecule
    0.303
    Number of heavy atoms
    49
    TPSA
    (Topological Polar Surface Area) 
    75.990 Å2
    Source organisms
    Peridinium bipes (Ref.494) - Alga: Dinoflagellate
    References
  • Ref.494 : Takashi MAOKA, Miyuki TSUSHIMA, and Hoyoku NISHINO, Chem. Pharm. Bull. 50(12) 1630—1633 (2002), "Isolation and Characterization of Dinochrome A and B, Anti-carcinogenic Active Carotenoids from the Fresh Water Red Tide Peridinium bipes".
  • Ref.569 : Maoka T, Tsushima M, Nishino H., Chem Pharm Bull 2002;50:1630–3., "Isolation and characterization of dinochrome A and B, anti-carcinogenic active carotenoids from the fresh water red tide, Peridinium bipes." .
  • CAS

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