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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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
    Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Phaeodactylum tricornutum (Ref.56)  - Alga: Diatom (Bacillariophyta - Phaeodactylaceae)
    Phaeodactylum tricornutum (Ref.56) - Alga: Diatom (Bacillariophyta - Phaeodactylaceae)
    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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