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Entry
CA00810                                                            

Classification
Carotenoid Name
Apo-12'-zeaxanthinal;
(3R)-3-Hydroxy-β-apo-12'-carotenal
IUPAC name (3R)-3-Hydroxy-12'-apo-beta-caroten-12'-al
Formula
C25H34O2
Molecular Weight 
366.522 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
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 
  • Constitutional isomer: CA00845
  • InChI
    InChI=1S/C25H34O2/c1-19(10-7-8-11-21(3)18-26)12-9-13-20(2)14-15-24-22(4)16-23(27)17-25(24,5)6/h7-15,18,23,27H,16-17H2,1-6H3/b8-7+,12-9+,15-14+,19-10+,20-13+,21-11+/t23-/m1/s1
    InChIKey
    PAUIQDPAEDELMC-HEZGKBSMSA-N
    Canonical SMILES
    O=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
    5.819
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.098
    Number of heavy atoms
    27
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Source organisms
    Nostoc sp. PCC 7120 (Ref.560) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Capsicum annuum L. (Ref.380) - Land plant: green pepper
    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.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.".
  • CAS
    62742-02-3
    Links to other DB
    KNApSAcK: C00022186

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