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Entry
CA00807                                                            
Classification
Carotenoid Name
Retinal;
Vitamin A aldehyde
IUPAC name 15-Apo-beta-caroten-15-al
Formula
C20H28O
Molecular Weight 
284.424 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Abolishes the function of the toxin Suberitine at a stoichiometric ratio of 1:1 (Ref.588).
  • Isomerized to 13Z-retinal under light, and isomerized back to all-trans retinal in the dark.
    • Number of
    conjugated double bonds 
    6 including one aldehyde (6 in total)
    Number of
    conjugated multiple bonds 
    6 including one aldehyde (6 in total)
    Isomers 
  • Constitutional isomer: CA01146, CA01149, CA01139
  • Cis/trans isomer: CA01034, CA01141
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    6.335
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.122
    Number of heavy atoms
    21
    TPSA
    (Topological Polar Surface Area) 
    17.070 Å2
    Reaction
  • Substrate: CR00217,  CR00259,  CR00433,  CR00444
  • Product: CR00023,  CR00024,  CR00028,  CR00030,  CR00050,  CR00053,  CR00060,  CR00388,  CR00445
    • Pathway
  • Pathway: CB000087,  CB000088,  CB000089,  CB000123
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Haloarcula japonica (Ref.621) - Archaea: Euryarchaeota, triangular, disc-shaped, extremely halophilic archaeon that requires high concentrations of NaCl for growth (Euryarchaeota - Halobacteriaceae)
    Mycobacterium tuberculosis (Ref.557) - Actinobacteria (Actinobacteria - Mycobacteriaceae)
    Nostoc sp. PCC 7120 (Ref.550, Ref.560) - Cyanobacteria: same as Anabaena sp. PCC 7120 (Cyanobacteria - Nostocaceae)
    Galleria mellonella (Ref.558) - Insect: greater wax moth (Arthropoda (Insecta) - Pyralidae)
    Suberites domuncula (Ref.588) - Sea sponge (Porifera - Suberitidae)
    Rana temporaria (Ref.420) - Common frog (Chordata - Ranidae)
    References
  • Ref.621: Ying Yang, Rie Yatsunami, Ai Ando, Nobuhiro Miyoko, Toshiaki Fukui, Shinichi Takaichi, Satoshi Nakamura, "Complete Biosynthetic Pathway of the C50 Carotenoid Bacterioruberin from Lycopene in the Extremely Halophilic Archaeon Haloarcula japonica", Journal of Bacteriology, May 2015 Volume 197 Number 9.
  • Ref.550: Erin K. Marasco, Kimleng Vay, and Claudia Schmidt-Dannert, THE JOURNAL OF BIOLOGICAL CHEMISTRY VOL. 281, NO. 42, pp. 31583–31593, October 20, 2006, "Identification of Carotenoid Cleavage Dioxygenases from Nostoc sp. PCC 7120 with Different Cleavage Activities".
  • 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.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" .
  • Ref.420: R. A. MORTON AND D. G. ROSEN, Biochem J. 1949; 45(5): 612–627., "Carotenoids, Vitamin A and 7-Dehydrosteroid in the Frog (Rana temporaria)".
  • Ref.588: Werner E. G. Müller, Xiaohong Wang, Michael Binder, Matthias Wiens, and Heinz C. Schröder, Mar. Drugs 2012, 10, 177-199; doi:10.3390/md10010177, ISSN 1660-3397, "Differential Expression of the Demosponge (Suberites domuncula) Carotenoid Oxygenases in Response to Light: Protection Mechanism Against the Self-Produced Toxic Protein (Suberitine)".
    • CAS
    116-31-4
    Links to other DB
    KEGG COMPOUND: C00376
    LipidBank: VVA0012

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