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Entry
CA00789                                                            

Classification
Carotenoid Name
Apo-8'-lycopenal
IUPAC name 8'-Apo-psi-caroten-8'-al
Formula
C30H40O
Molecular Weight 
416.62 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
10 including one aldehyde (10 in total)
Number of
conjugated multiple bonds 
10 including one aldehyde (10 in total)
Isomers 
  • Constitutional isomer: CA00011, CA00825
  • InChI
    InChI=1S/C30H40O/c1-25(2)14-10-17-28(5)19-12-21-29(6)20-11-18-26(3)15-8-9-16-27(4)22-13-23-30(7)24-31/h8-9,11-16,18-24H,10,17H2,1-7H3/b9-8+,18-11+,21-12+,22-13+,26-15+,27-16+,28-19+,29-20+,30-23+
    InChIKey
    AQXFMDSHWVVBIM-DCLDNXSWSA-N
    Canonical SMILES
    O=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(/CCC=C(C)C)\C)\C)\C)/C)/C
    XLogP
    9.610
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    31
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Source organisms
    Nostoc sp. PCC 7120 (Ref.560) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Lycopersicon esculentum (Ref.346) - Land plant: Solanaceae: tomato
    Fusarium fujikuroi (Ref.555) - Fungi: ascomycete fungus
    References
  • Ref.560 : Scherzinger D, Ruch S, Kloer DP, Wilde A, Al-Babili S., Biochem J. 2006 Sep 15;398(3):361-9., PMID: 16759173 PMCID: PMC1559462 DOI: 10.1042/BJ20060592, "Retinal is formed from apo-carotenoids in Nostoc sp. PCC7120: in vitro characterization of an apo-carotenoid oxygenase.".
  • Ref.346 : Avraham Ben-Aziz, George Britton, Trevor W. Goodwin, Phytochemistry, Volume 12, Issue 11, November 1973, Pages 2759-2764, "Carotene epoxides of Lycopersicon esculentum".
  • Ref.555 : Alfonso Prado-Cabrero,Alejandro F. Estrada, Salim Al-Babili and Javier Avalos, Molecular Microbiology (2007) 64(2), 448–460, doi:10.1111/j.1365-2958.2007.05665.x, "Identification and biochemical characterization of anovel carotenoid oxygenase: elucidation of thecleavage step in theFusarium carotenoid pathway".
  • CAS
    2213-22-1
    Links to other DB
    KNApSAcK: C00023119

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