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Entry
CA00818                                                            

Classification
Carotenoid Name
Apo-12'-fucoxanthinal
IUPAC name (3S,5R,6S)-5,6-Epoxy-3-hydroxy-8-oxo-5,6,7,8-tetrahydro-12'-apo-beta-caroten-12'-al
Formula
C25H34O4
Molecular Weight 
398.522 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 ketone and one aldehyde (7 in total)
    Number of
    conjugated multiple bonds 
    7 including one ketone and one aldehyde (7 in total)
    Isomers 
    InChI
    InChI=1S/C25H34O4/c1-18(10-7-8-11-19(2)17-26)12-9-13-20(3)22(28)16-25-23(4,5)14-21(27)15-24(25,6)29-25/h7-13,17,21,27H,14-16H2,1-6H3/b8-7+,12-9+,18-10+,19-11+,20-13+/t21-,24+,25-/m0/s1
    InChIKey
    MFXMPUIXRGTKOU-XTGOMCJVSA-N
    Canonical SMILES
    O=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
    3.834
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    0
    Complexity of molecule
    0.111
    Number of heavy atoms
    29
    TPSA
    (Topological Polar Surface Area) 
    66.900 Å2
    Source organisms
    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
    22488-61-5
    Links to other DB
    KNApSAcK: C00023132

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