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Entry
CA00828                                                            

Classification
Carotenoid Name
Apo-12-fucoxanthinal
IUPAC name (3S,5R,6R)-3-ethanoyloxy-5-hydroxy-6,7-didehydro-5,6-dihydro-12'-apo-beta-caroten-12'-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 
    7 including one aldehyde (7 in total)
    Number of
    conjugated multiple bonds 
    7 including one aldehyde (7 in total)
    Isomers 
  • Constitutional isomer: CA00827
  • InChI
    InChI=1S/C27H36O4/c1-20(11-8-9-12-22(3)19-28)13-10-14-21(2)15-16-25-26(5,6)17-24(31-23(4)29)18-27(25,7)30/h8-15,19,24,30H,17-18H2,1-7H3/b9-8+,13-10+,20-11+,21-14+,22-12+/t16?,24-,27+/m0/s1
    InChIKey
    VUTCKOBMFJDHLW-ZATHBAGMSA-N
    Canonical SMILES
    O=C/C(=C/C=C/C=C(/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)\C)\C)/C
    XLogP
    7.114
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.090
    Number of heavy atoms
    31
    TPSA
    (Topological Polar Surface Area) 
    63.600 Å2
    Source organisms

    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
    22488-58-0
    Links to other DB

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