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Entry
CA00493                                                            

Classification
Carotenoid Name
4'-Hydroxy-4-ketoalloxanthin
IUPAC name (3S,3'S,4'R)-3,3',4'-Trihydroxy-7,8,7',8'-tetrahydro-beta,beta-caroten-4-one
Formula
C40H50O4
Molecular Weight 
594.8 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
7 and 2 including one ketone (9 in total)
Number of
conjugated multiple bonds 
12 including one ketone (12 in total)
Isomers 
  • Constitutional isomer: CA00495, CA00548, CA00494
  • InChI
    InChI=1S/C40H50O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-20,35-37,41-43H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,27-15+,28-16+,29-19+,30-20+/t35-,36-,37+/m0/s1
    InChIKey
    LXUQYKJMQWQSFH-ZYVPYCLYSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C#CC1=C(C)C(=O)[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C#CC1=C(C)[C@@H](O)[C@H](CC1(C)C)O)\C
    XLogP
    9.305
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.319
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    77.760 Å2
    Source organisms
    Clione limacina (Ref.635) - gastropods
    Paedoclione doliiformis (Ref.635) - gastropods
    References
  • Ref.635 : Takashi Maoka, Takashi Kuwahara, and Masanao Narita, Mar. Drugs 2014, 12, 1460-1470, "Carotenoids of Sea Angels Clione limacina and Paedoclione doliiformis from the Perspective of the Food Chain", doi:10.3390/md12031460.
  • CAS
    253264-74-3
    Links to other DB
    KNApSAcK: C00023017

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