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Entry
CA01031                                                            

Classification
Carotenoid Name
Vitamin A;
Vitamin A1;
Vitamin A alchol;
Retinol;
all-trans-Retinol
IUPAC name 15-Apo-beta-caroten-15-ol
Formula
C20H30O
Molecular Weight 
286.44 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity (Ref.487).
  • Absorpsion maxim: λmax in UV: 328nm λmax: 617nm (Ref.571).
  • Number of
    conjugated double bonds 
    5
    Number of
    conjugated multiple bonds 
    5
    Isomers 
  • Cis/trans isomer: CA01032, CA01033
  • InChI
    InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
    InChIKey
    FPIPGXGPPPQFEQ-OVSJKPMPSA-N
    Canonical SMILES
    OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
    XLogP
    6.158
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.118
    Number of heavy atoms
    21
    TPSA
    (Topological Polar Surface Area) 
    20.230 Å2
    Source organisms
    Homo sapiens (Ref.422) - Human
    References
  • Ref.422 : Dean Bok, Joram Heller, Experimental Eye Research, Volume 22, Issue 5, Part 1, May 1976, Pages 395-402, "Transport of retinol from the blood to the retina: an autoradiographic study of the pigment epithelial cell surface receptor for plasma retinol-binding protein".
  • Ref.487 : Bertram JS, Vine AL., Biochim Biophys Acta. 2005 May 30;1740(2):170-8. Epub 2005 Jan 25., "Cancer prevention by retinoids and carotenoids: independent action on a common target.".
  • Ref.571 : Morton RA, Creed RH., Biochem J. 1939 Mar;33(3):318-24., PMID: 16746914 PMCID: PMC1264377, "The conversion of carotene to vitamin A(2) by some fresh-water fishes.".
  • CAS
    68-26-8
    Links to other DB

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