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Entry
CA01000                                                            
Classification
Carotenoid Name
Apo-15-zeaxanthinal;
(all-E)-3-Hydroxy-retinal
IUPAC name (3R)-3-Hydroxy-15-apo-beta-caroten-15-al
Formula
C20H28O2
Molecular Weight 
300.424 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Essential for photoreceptor cell function and survival (Ref.558).
    • Number of
    conjugated double bonds 
    6 including one aldehyde (8 in total)
    Number of
    conjugated multiple bonds 
    6 including one aldehyde (8 in total)
    Isomers 
  • Constitutional isomer: CA01221, CA01045, CA01036, CA01140
  • Cis/trans isomer: CA01142
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    4.250
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    0
    Complexity of molecule
    0.120
    Number of heavy atoms
    22
    TPSA
    (Topological Polar Surface Area) 
    37.300 Å2
    Reaction
  • Product: CR00022,  CR00025,  CR00026,  CR00027,  CR00051,  CR00052,  CR00062,  CR00415
    • Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Mycobacterium tuberculosis (Ref.557) - Actinobacteria (Actinobacteria - Mycobacteriaceae)
    Nostoc sp. PCC 7120 (Ref.560) - Cyanobacteria: same as Anabaena sp. PCC 7120 (Cyanobacteria - Nostocaceae)
    Capsicum annuum L. (Ref.380) - Land plant: green pepper (Streptophyta - Solanaceae)
    Galleria mellonella (Ref.558) - Insect: greater wax moth (Arthropoda (Insecta) - Pyralidae)
    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.".
  • Ref.558: Vitus Oberhausera, Olaf Voolstraa, Annette Bangerta, Johannes von Lintigb, and Klaus Vogt, Proc Natl Acad Sci U S A. 2008 Dec 2;105(48):19000-5. doi: 10.1073/pnas.0807805105. Epub 2008 Nov 19., "NinaB combines carotenoid oxygenase and retinoid isomerase activity in a single polypeptide.".
  • 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
    60046-53-9
    Links to other DB

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