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Entry
CA00844                                                            

Classification
Carotenoid Name
β-Apo-12'-carotenal;
beta-Apo-12'-carotenal;
12'-apo-Carotenal
IUPAC name 12'-Apo-beta-caroten-12'-al
Formula
C25H34O
Molecular Weight 
350.522 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Induce cell cycle arrest in cancer cells (Ref.415).
  • Number of
    conjugated double bonds 
    8 including one aldehyde (8 in total)
    Number of
    conjugated multiple bonds 
    8 including one aldehyde (8 in total)
    Isomers 
    InChI
    InChI=1S/C25H34O/c1-20(11-7-8-12-22(3)19-26)13-9-14-21(2)16-17-24-23(4)15-10-18-25(24,5)6/h7-9,11-14,16-17,19H,10,15,18H2,1-6H3/b8-7+,13-9+,17-16+,20-11+,21-14+,22-12+
    InChIKey
    BQTOMHXDSCUCFR-PHPDKTIJSA-N
    Canonical SMILES
    O=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)/C
    XLogP
    7.904
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.100
    Number of heavy atoms
    26
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Cucumis melo Inodorus Group (Ref.392)  - Land plant: orange-fleshed muskmelon "honeydew"
    References
  • Ref.392 : Fleshman, Matthew K.; Lester, Gene E.; Riedl, Ken M.; Kopec, Rachel E.; Narayanasamy, Sureshbabu; Curley, Robert W.; Schwartz, Steven J.; Harrison, Earl H., Journal of Agricultural and Food Chemistry (2011), 59(9), 4448-4454., "Carotene and Novel Apocarotenoid Concentrations in Orange-Fleshed Cucumis melo Melons: Determinations of β-Carotene Bioaccessibility and Bioavailability".
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • CAS
    1638-05-7
    Links to other DB
    KEGG COMPOUND: C19812

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