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Entry
CA00827                                                            

Classification
Carotenoid Name
Apo-10'-fucoxanthinal
IUPAC name (3S,5R,6S)-5,6-Epoxy-3-hydroxy-8-oxo-5,6,7,8-tetrahydro-10'-apo-beta-caroten-10'-al
Formula
C27H36O4
Molecular Weight 
424.558 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Feeding deterrent activity against a copepod (Ref.56, Ref.232).
  • Number of
    conjugated double bonds 
    8 including one ketone and one aldehyde (8 in total)
    Number of
    conjugated multiple bonds 
    8 including one ketone and one aldehyde (8 in total)
    Isomers 
  • Constitutional isomer: CA00828
  • InChI
    InChI=1S/C27H36O4/c1-20(11-7-8-12-21(2)14-10-16-28)13-9-15-22(3)24(30)19-27-25(4,5)17-23(29)18-26(27,6)31-27/h7-16,23,29H,17-19H2,1-6H3/b8-7+,13-9+,14-10+,20-11+,21-12+,22-15+/t23-,26+,27-/m0/s1
    InChIKey
    HQQUWEPSOVTLND-VEFZEHLJSA-N
    Canonical SMILES
    O=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C)\C)/C
    XLogP
    4.739
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    0
    Complexity of molecule
    0.104
    Number of heavy atoms
    31
    TPSA
    (Topological Polar Surface Area) 
    66.900 Å2
    Source organisms
    Phaeodactylum tricornutum (Ref.56) - Alga: Diatom
    Phaeodactylum tricornutum (Ref.56) - Alga: Diatom
    Phaeodactylum tricornutum (Ref.56)  - Alga: Diatom
    References
  • Ref.56 : B. A. Shaw, R. J. Anderson, P. J. Harrison, Marine Biology (1995) 124:467-472, "Feeding deterrence properties of apo-fucoxanthinoids from marine diatoms. I. Chemical structures of apo-fucoxanthinoids produced by Phaeodactylum tricornutum".
  • Ref.232 : Shaw, B. A.; Andersen, R. J.; Harrison, P. J., Marine Biology (Berlin) (1997), 128(2), 273-280., "Feeding deterrent and toxicity effects of apo-fucoxanthinoids and phycotoxins on a marine copepod (Tigriopus californicus)".
  • CAS
    22488-62-6
    Links to other DB
    KNApSAcK: C00023127

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