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Entry
CA00846                                                            

Classification
Carotenoid Name
Apo-10'-zeaxanthinal
IUPAC name 3-Hydroxy-10'-apo-beta-caroten-10'-al
Formula
C27H36O2
Molecular Weight 
392.558 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including one aldehyde (9 in total)
Number of
conjugated multiple bonds 
9 including one aldehyde (9 in total)
Isomers 
  • Constitutional isomer: CA00795, CA00847
  • InChI
    InChI=1S/C27H36O2/c1-21(11-7-8-12-22(2)15-10-18-28)13-9-14-23(3)16-17-26-24(4)19-25(29)20-27(26,5)6/h7-18,25,29H,19-20H2,1-6H3/b8-7+,13-9+,15-10+,17-16+,21-11+,22-12+,23-14+/t25-/m1/s1
    InChIKey
    HQPQTQQUHPFUOA-ZCPYHVQDSA-N
    Canonical SMILES
    O=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)C[C@H](CC1(C)C)O)\C)\C)/C
    XLogP
    6.724
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.092
    Number of heavy atoms
    29
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Sinton citrangequat  - Land plant: citrus hybrid of a citrange and a kumquat
    Capsicum annuum L. (Ref.380) - Land plant: green pepper
    Mycobacterium tuberculosis (Ref.557) - Actinobacteria
    References
  • Ref.380 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry¬†(2001),¬†49(3),¬†1601-1606., "Isolation of a Series of Apocarotenoids from the Fruits of the Red Paprika Capsicum annuum L.".
  • Ref.557 : Daniel Scherzinger, Erdmann Scheffer, Cornelia Bar, Hansgeorg Ernst and Salim Al-Babili, FEBS J. 2010 Nov;277(22):4662-73. doi: 10.1111/j.1742-4658.2010.07873.x. Epub 2010 Oct 4."The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids" .
  • CAS
    62742-01-2
    Links to other DB
    KNApSAcK: C00022185
    MassBank: CA000011

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