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Entry
CA00505                                                            

Classification
Carotenoid Name
Xipholenin
IUPAC name (3S,3'S,6'R)-3-Methoxy-3'-hydroxy-beta,epsilon-caroten-4-one
Formula
C41H56O3
Molecular Weight 
596.858 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
11 including one ketone (11 in total)
Number of
conjugated multiple bonds 
11 including one ketone (11 in total)
Isomers 
  • Constitutional isomer: CA00186, CA00253
  • InChI
    InChI=1S/C41H56O3/c1-29(18-14-20-31(3)22-24-36-33(5)26-35(42)27-40(36,7)8)16-12-13-17-30(2)19-15-21-32(4)23-25-37-34(6)39(43)38(44-11)28-41(37,9)10/h12-26,35-36,38,42H,27-28H2,1-11H3/b13-12+,18-14+,19-15+,24-22+,25-23+,29-16+,30-17+,31-20+,32-21+/t35-,36+,38+/m1/s1
    InChIKey
    XMJZUQVGBMNPFZ-KGYDGMHDSA-N
    Canonical SMILES
    CO[C@H]1CC(C)(C)C(=C(C1=O)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@H]1C(=C[C@H](CC1(C)C)O)C)\C)\C)/C)/C
    XLogP
    10.939
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    2
    Complexity of molecule
    0.300
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    46.530 Å2
    Source organisms
    Xipholena punicea (Ref.272) - Bird: pompadour cotinga
    References
  • Ref.272 : Amy M. LaFountain, Shanti Kaligotla, Shannon Cawley, Ken M. Riedl, Steven J. Schwartz, Harry A. Frank, and Richard O. Prum, Arch Biochem Biophys. 2010 Dec 1; 504(1): 10.1016/j.abb.2010.08.006., doi: 10.1016/j.abb.2010.08.006, "Novel methoxy-carotenoids from the burgundy-colored plumage of the Pompadour Cotinga Xipholena punicea".
  • CAS
    1356476-26-0
    Links to other DB

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