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Entry
CA01045                                                            

Classification
Carotenoid Name
4-Oxoretinol;
all-trans-4-Oxoretinol;
Retin-4-one, 15-hydroxy
IUPAC name 4-oxo-15-apo-beta-caroten-15-ol
Formula
C20H28O2
Molecular Weight 
300.424 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Activate transcription of the retinoic acid receptors (Ref.423).
  • Number of
    conjugated double bonds 
    6 including one ketone (6 in total)
    Number of
    conjugated multiple bonds 
    6 including one ketone (6 in total)
    Isomers 
  • Constitutional isomer: CA01036, CA01000, CA01140
  • InChI
    InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+
    InChIKey
    PLIUCYCUYQIBDZ-RMWYGNQTSA-N
    Canonical SMILES
    OC/C=C(/C=C/C=C(/C=C/C1=C(C)C(=O)CCC1(C)C)\C)\C
    XLogP
    4.185
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    0
    Complexity of molecule
    0.120
    Number of heavy atoms
    22
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms

    References
  • Ref.423 : CHARLES C. ACHKAR, FADILA DERGUINI, BRUCE BLUMBERG, ALEXANDER LANGSTON, ARTHUR A. LEVINTII, JEFFREY SPECKS, RONALD M. EVANS, JACK BOLADO, JR., KoJi NAKANISHI, JOCHEN BUCK, AND LORRAINE J. GUDAS, Proc. Natl. Acad. Sci. USA Vol. 93, pp. 4879-4884, May 1996 Pharmacology, "4-Oxoretinol, a new natural ligand and transactivator of the retinoic acid receptors".
  • CAS
    62702-55-0
    Links to other DB

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