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Entry
CA00578                                                            

Classification
Carotenoid Name
Pyrrhoxanthin
IUPAC name (3S,5R,6S,3'R)-5,6-Epoxy-3'-ethanoyloxy-3-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: CA00982, CA00968, CA00675
  • InChI
    InChI=1S/C39H48O6/c1-26(16-17-34-28(3)21-33(43-29(4)40)25-36(34,5)6)14-12-10-11-13-15-27(2)20-32-22-30(35(42)44-32)18-19-39-37(7,8)23-31(41)24-38(39,9)45-39/h10-15,18-20,22,31,33,41H,21,23-25H2,1-9H3/b12-10+,13-11+,19-18+,26-14+,27-15+,32-20-/t31-,33+,38+,39-/m0/s1
    InChIKey
    YDSRGWPRPWTZCK-CHOIYNEVSA-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@]2(C)C[C@H](CC1(C)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) 
    85.360 Å2
    Source organisms
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate
    Gyrodinium dorsum (Ref.33) - Alga: Dinoflagellate
    Glenodinium sp. (Ref.33) - Alga: Dinoflagellate
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    References
  • Ref.33 : J. E. Joansen, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1974, Vol.13 pp.2261-2271, "Carotenoids of the Dinophyceae".
  • 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)".
  • CAS
    54369-13-0
    Links to other DB
    KNApSAcK: C00023162
    LipidBank: VCA0006

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