Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00413   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00413                                                            

Classification
Carotenoid Name
Peridininol 5,8-furanooxide
IUPAC name (3S,5R,6S,3'S,5'R,6'S)-5,8-Epoxy-3,3',5'-trihydroxy-5,6,5',6'-tetrahydro-6',7'-didehydro-beta,beta-caroten-19,11-olide
Formula
C37H48O6
Molecular Weight 
588.754 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - significant growth-inhibitory activity toward cancer cells - antiproliferative activity (Ref.568).
  • Number of
    conjugated double bonds 
    8 including one lactone (8 in total)
    Number of
    conjugated multiple bonds 
    8 including one lactone (8 in total)
    Isomers 
  • Constitutional isomer: CA00577, CA00576
  • InChI
    InChI=1S/C37H48O6/c1-24(15-16-31-34(3,4)20-26(38)22-36(31,7)41)13-11-9-10-12-14-25(2)17-28-18-29(33(40)42-28)30-19-32-35(5,6)21-27(39)23-37(32,8)43-30/h9-15,17-19,26-27,30,38-39,41H,20-23H2,1-8H3/b11-9+,12-10+,24-13+,25-14+,28-17-/t16-,26-,27-,30?,36+,37+/m0/s1
    InChIKey
    RWIFCBRKLSVYBB-WSUGZHIRSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C\C=C(\C=C/1\C=C(C(=O)O1)C1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)/C)/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O
    XLogP
    6.925
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    6
    LipinskiFailures
    1
    Complexity of molecule
    0.341
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    96.220 Å2
    Source organisms
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    References
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • Ref.568 : Suzuki M, Watanabe K, Fujiwara S, Kurasawa T, Wakabayashi T, Tsuzuki M, et al., Chem Phrm Bull 2003;51:724–7. "Isolation of peridinin-related norcarotenoids with cell growth-inhibitory activity from the cultured dinoflagellate of Symbiodinium sp., a symbiont of the Okinawan soft coral Clavularia virdis, and analysis of fatty acid of the dinoflagellate." .
  • CAS
    1361568-40-2
    Links to other DB
    MassBank: CA000093

       Search other references with Google Scholar