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Entry
CA01142                                                            

Classification
Carotenoid Name
(11Z)-3-Hydroxyretinal
IUPAC name (11Z,3R)-3-Hydroxy-15-apo-beta-caroten-15-al
Formula
C20H28O2
Molecular Weight 
300.424 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Visual chromophore essential for photoreceptor cell function and survival generally found in insects. Essential for insect vision (Ref.558, Ref.572, Ref.573).
  • 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 
  • Cis/trans isomer: CA01000
  • InChI
    InChI=1S/C20H28O2/c1-15(7-6-8-16(2)11-12-21)9-10-19-17(3)13-18(22)14-20(19,4)5/h6-12,18,22H,13-14H2,1-5H3/b8-6-,10-9+,15-7+,16-11+/t18-/m1/s1
    InChIKey
    QPRQNCDEPWLQRO-NIKQCJNBSA-N
    Canonical SMILES
    O=C/C=C(/C=C\C=C(\C=C\C1=C(C)C[C@H](CC1(C)C)O)/C)\C
    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
    Source organisms
    Galleria mellonella (Ref.558) - Insect: greater wax moth
    References
  • 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.572 : Vogt, K. (1989). "Distribution of insect visual chromophores: functional and phylogenetic aspects.", In Facets of Vision, D.G. Stavenga and R.C. Hardie,eds. (Berlin, Heidelberg: Springer), pp. 134–151..
  • Ref.573 : Darwin Babino, Marcin Golczak, Philip D. Kiser, Adrian Wyss, Krzysztof Palczewski, and Johannes von Lintig, ACS Chem Biol. 2016 Apr 15;11(4):1049-57. doi: 10.1021/acschembio.5b00967. Epub 2016 Feb 2., PMID: 26811964 PMCID: PMC4841470 [Available on 2017-04-15] DOI: 10.1021/acschembio.5b00967, "The Biochemical Basis of Vitamin A3 Production in Arthropod Vision".
  • CAS

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