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Entry
CA01003                                                            

Classification
Carotenoid Name
Apo-13-zeaxanthinone
IUPAC name (3R)-3-Hydroxy-13-apo-beta-caroten-13-one
Formula
C18H26O2
Molecular Weight 
274.388 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
5 including one ketone (5 in total)
Number of
conjugated multiple bonds 
5 including one ketone (5 in total)
Isomers 
  • Constitutional isomer: CA00869
  • InChI
    InChI=1S/C18H26O2/c1-13(7-6-8-15(3)19)9-10-17-14(2)11-16(20)12-18(17,4)5/h6-10,16,20H,11-12H2,1-5H3/b8-6+,10-9+,13-7+/t16-/m1/s1
    InChIKey
    JLNMEHQAHDSEEE-YSAUQHOWSA-N
    Canonical SMILES
    O[C@@H]1CC(=C(C(C1)(C)C)/C=C/C(=C/C=C/C(=O)C)/C)C
    XLogP
    3.345
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    0
    Complexity of molecule
    0.130
    Number of heavy atoms
    20
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    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
    336105-81-8
    Links to other DB
    KNApSAcK: C00022189

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