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Entry
CA01204                                                            

Classification
Carotenoid Name
(13Z)-Retinoic acid: 13-cis-Retinoic acid;
13-cis-Retinoate
IUPAC name (13Z)-15-Apo-beta-caroten-15-oic acid
Formula
C20H28O2
Molecular Weight 
300.424 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - clinically used to treat acute promyelocytic leukaemia, skin diseases, and cancer. (Ref.631)
  • Number of
    conjugated double bonds 
    6 including one carboxylic acid (6 in total)
    Number of
    conjugated multiple bonds 
    6 including one carboxylic acid (6 in total)
    Isomers 
  • Cis/trans isomer: CA01036, CA01035
  • InChI
    InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
    InChIKey
    SHGAZHPCJJPHSC-XFYACQKRSA-N
    Canonical SMILES
    C/C(=C\C=C\C(=C/C(=O)O)\C)/C=C/C1=C(C)CCCC1(C)C
    XLogP
    6.254
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.120
    Number of heavy atoms
    22
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Homo sapiens (Ref.631) - Human
    References
  • Ref.631 : Yusuke Takahashi, Gennadiy Moiseyev, Ying Chen, Krysten Farjo, Olga Nikolaeva, and Jian-xing Ma, FEBS J. Author manuscript; available in PMC 2012 April 1. "An Enzymatic Mechanism for Generating the Precursor of Endogenous 13-cis Retinoic Acid in the Brain".
  • CAS

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