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Entry
CA00809                                                            

Classification
Carotenoid Name
Apo-13'-fucoxanthinone
IUPAC name (3S,5R,6R)-3-ethanoyloxy-5-hydroxy-6,7-didehydro-5,6-dihydro-13-apo-beta-caroten-13-al
Formula
C20H28O4
Molecular Weight 
332.424 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 
    4 including one ketone (4 in total)
    Number of
    conjugated multiple bonds 
    4 including one ketone (4 in total)
    Isomers 
    InChI
    InChI=1S/C20H28O4/c1-14(8-7-9-15(2)21)10-11-18-19(4,5)12-17(24-16(3)22)13-20(18,6)23/h7-10,17,23H,12-13H2,1-6H3/b9-7+,14-8+/t11?,17-,20+/m0/s1
    InChIKey
    ZOBVTHBOBODYBD-IFTLXNJVSA-N
    Canonical SMILES
    C/C(=C\C=C\C(=O)C)/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C
    XLogP
    4.640
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    0
    Complexity of molecule
    0.115
    Number of heavy atoms
    24
    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
    183182-96-9
    Links to other DB

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