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Carotenoids DB          Carotenoids DB: CA01149   
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Entry
CA01149                                                            
Classification
Carotenoid Name
Vitamin A2;
3,4-Didehydro-all-trans-retinol;
3-dehydroretinol
IUPAC name 15-Apo-3,4-didehydro-beta-caroten-15-ol
Formula
C20H28O
Molecular Weight 
284.424 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Converted from Vitamin A1 by CYP450 family Cyp27c1 (Ref.570).
  • Absorpsion maxim: λmax in UV: 350nm λmax: 693nm (Ref.571).
    • Number of
    conjugated double bonds 
    6
    Number of
    conjugated multiple bonds 
    6
    Isomers 
  • Constitutional isomer: CA01146, CA00807, CA01139
    • InChI

    InChIKey

    Canonical SMILES

    XLogP
    6.044
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.122
    Number of heavy atoms
    21
    TPSA
    (Topological Polar Surface Area) 
    20.230 Å2
    Reaction
  • Product: CR00100
    • Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Leuciscus leuciscus (Ref.571) - Bony fish: dace, Eurasian dace (Chordata - Cyprinidae)
    Perca fluviatilis (Ref.571) - Bony fish: European perch (Chordata - Percidae)
    Bagarius bagarius (Ref.580) - Bony fish: dwarf goonch (Chordata - Sisoridae)
    Wallago attu (Ref.580) - Bony fish (Chordata - Siluridae)
    References
  • Ref.570: Enright JM, Toomey MB, Sato SY, Temple SE, Allen JR, Fujiwara R, Kramlinger VM, Nagy LD, Johnson KM, Xiao Y, How MJ, Johnson SL, Roberts NW, Kefalov VJ, Guengerich FP, Corbo JC., Curr Biol. 2015 Dec 7;25(23):3048-57. doi: 10.1016/j.cub.2015.10.018. Epub 2015 Nov 5., PMID: 26549260 PMCID: PMC4910640 [Available on 2016-12-07] DOI: 10.1016/j.cub.2015.10.018, "Cyp27c1 Red-Shifts the Spectral Sensitivity of Photoreceptors by Converting Vitamin A1 into A2.".
  • Ref.571: Morton RA, Creed RH., Biochem J. 1939 Mar;33(3):318-24., PMID: 16746914 PMCID: PMC1264377, "The conversion of carotene to vitamin A(2) by some fresh-water fishes.".
  • Ref.580: ARUN B. BARUA, RATHIN C. DAS and KAMNA VERMA, Biochem. J. (1977) 168, 557-564, "Occurrence of 3-Hydroxyretinol in the Freshwater Fish Bagarius bagarius and Wallago attu ISOLATION AND SYNTHESIS".
    • CAS

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