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Entry
CA00428                                                            

Classification
Carotenoid Name
Peridinine 5,8-furanoside;
Peridinine 5,8-furanooxide;
Nor-peridinin
IUPAC name (3S,5R,6S,3'S,5'R,6'S)-5,8-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-5,6,5',6'-tetrahydro-6',7'-didehydro-beta,beta-caroten-19,11-olide
Formula
C39H50O7
Molecular Weight 
630.79 g/mol
Structure      Search similar carotenoids

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 
  • Conformer: CA01087, CA01088
  • Constitutional isomer: CA00579
  • InChI
    InChI=1S/C39H50O7/c1-25(16-17-33-37(6,7)23-30(44-27(3)40)24-38(33,8)43)14-12-10-11-13-15-26(2)18-29-19-31(35(42)45-29)32-20-34-36(4,5)21-28(41)22-39(34,9)46-32/h10-16,18-20,28,30,32,41,43H,21-24H2,1-9H3/b12-10+,13-11+,25-14+,26-15+,29-18-/t17-,28-,30-,32?,38+,39+/m0/s1
    InChIKey
    KQQRQKINDGGYIE-WMEAYEIZSA-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)OC(=O)C
    XLogP
    7.665
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    7
    LipinskiFailures
    1
    Complexity of molecule
    0.323
    Number of heavy atoms
    46
    TPSA
    (Topological Polar Surface Area) 
    102.290 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
    59444-24-5
    Links to other DB

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