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Entry
CA00573                                                            

Classification
Carotenoid Name
Pyrrhoxanthinol
IUPAC name (3S,5R,6S,3'R)-5,6-Epoxy-3,3'-dihydroxy-7',8'-dihydro-5,6-dihydro-12',13',20'-trinor-beta,beta-caroten-19,11-olide
Formula
C37H46O5
Molecular Weight 
570.738 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: CA00967
  • InChI
    InChI=1S/C37H46O5/c1-25(15-16-32-27(3)20-29(38)22-34(32,4)5)13-11-9-10-12-14-26(2)19-31-21-28(33(40)41-31)17-18-37-35(6,7)23-30(39)24-36(37,8)42-37/h9-14,17-19,21,29-30,38-39H,20,22-24H2,1-8H3/b11-9+,12-10+,18-17+,25-13+,26-14+,31-19-/t29-,30+,36-,37+/m1/s1
    InChIKey
    JPHOIGCQEIPBBI-RHYXJIAFSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C\C=C(\C#CC1=C(C)C[C@H](CC1(C)C)O)/C)/C=C/1\OC(=O)C(=C1)/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O
    XLogP
    6.920
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    1
    Complexity of molecule
    0.352
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    79.290 Å2
    Source organisms
    Gyrodinium dorsum (Ref.33) - Alga: Dinoflagellate
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sp. (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
    54369-11-8
    Links to other DB
    KNApSAcK: C00023161
    MassBank: CA000097

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