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Entry
CA01036                                                            

Classification
Carotenoid Name
(all-E)-Retinoic acid;
all-trans-Retinoate;
all-trans-Vitamin A acid
IUPAC name 15-Apo-beta-caroten-15-oic acid
Formula
C20H28O2
Molecular Weight 
300.424 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Induce cell differentiation (Ref.423).
  • Anticarcinogenic activity against many target organs including mammary gland, urinary bladder, lung, skin, liver, pancreas, colon and esophagus (Ref.486).
  • 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 
  • Constitutional isomer: CA01045, CA01000, CA01140
  • Cis/trans isomer: CA01035, CA01204
  • 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-YCNIQYBTSA-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

    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".
  • Ref.486 : Moon RC, J Nutr. 1989 Jan;119(1):127-34., PMID: 2643696, "Comparative aspects of carotenoids and retinoids as chemopreventive agents for cancer.".
  • CAS
    5300-03-8
    Links to other DB

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