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Entry
CA00982                                                            

Classification
Carotenoid Name
Cyclopyrrhoxanthin
IUPAC name (3S,5R,6R,3'R)-3,6-Epoxy-3'-ethanoyloxy-5-hydroxy-7',8'-didehydro-5,6-dihydro-12',13',20'-trinor-beta,beta-caroten-19,11-olide
Formula
C39H48O6
Molecular Weight 
612.774 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
8 including one lactone (8 in total)
Number of
conjugated multiple bonds 
10 including one lactone (10 in total)
Isomers 
  • Constitutional isomer: CA00968, CA00578, CA00675
  • InChI
    InChI=1S/C39H48O6/c1-26(16-17-34-28(3)21-32(43-29(4)40)23-36(34,5)6)14-12-10-11-13-15-27(2)20-31-22-30(35(41)44-31)18-19-39-37(7,8)24-33(45-39)25-38(39,9)42/h10-15,18-20,22,32-33,42H,21,23-25H2,1-9H3/b12-10+,13-11+,19-18+,26-14+,27-15+,31-20-/t32-,33+,38-,39-/m1/s1
    InChIKey
    GRBTZPLUNSWVPO-YOZNXODWSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C\C=C(\C=C/1\C=C(C(=O)O1)/C=C/[C@@]12O[C@H](CC1(C)C)C[C@@]2(C)O)/C)/C#CC1=C(C)C[C@H](CC1(C)C)OC(=O)C
    XLogP
    7.660
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    6
    LipinskiFailures
    1
    Complexity of molecule
    0.333
    Number of heavy atoms
    45
    TPSA
    (Topological Polar Surface Area) 
    82.060 Å2
    Source organisms
    Corbicula japonica (Ref.221, Ref.515) - 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.515 : Takashi Maoka, Archives of Biochemistry and Biophysics 483 (2009) 191–195, "Recent progress in structural studies of carotenoids in animals and plants".
  • CAS
    866025-62-9
    Links to other DB

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