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Entry
CA01135                                                            

Classification
Carotenoid Name
(9Z,3S,5R,6S)-5,6-Epoxy-3-hydroxy-12'-apo-β-caroten-12'-al;
(9Z,3S,5R,6S)-5,6-Epoxy-3-hydroxy-12'-apo-beta-caroten-12'-al;
C27 epoxy-apocarotenal
IUPAC name (9Z,3S,5R,6S)-5,6-Epoxy-3-hydroxy-12'-apo-beta-caroten-12'-al
Formula
C25H34O3
Molecular Weight 
382.522 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
7 including one aldehyde (7 in total)
Number of
conjugated multiple bonds 
7 including one aldehyde (7 in total)
Isomers 
  • Cis/trans isomer: CA00841
  • InChI
    InChI=1S/C25H34O3/c1-19(10-7-8-11-21(3)18-26)12-9-13-20(2)14-15-25-23(4,5)16-22(27)17-24(25,6)28-25/h7-15,18,22,27H,16-17H2,1-6H3/b8-7+,12-9+,15-14+,19-10+,20-13-,21-11+/t22-,24+,25-/m0/s1
    InChIKey
    CAXVJDRXJFKYQP-AXMRWBPPSA-N
    Canonical SMILES
    O=C/C(=C/C=C/C=C(/C=C/C=C(\C=C\[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)\C)/C
    XLogP
    5.019
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    1
    Complexity of molecule
    0.113
    Number of heavy atoms
    28
    TPSA
    (Topological Polar Surface Area) 
    49.830 Å2
    Source organisms
    Arabidopsis thaliana (Ref.551) - Land plant: thale-cress, a model organism
    References
  • Ref.551 : Steven H. Schwartz, Xiaoqiong Qin, and Jan A. D. Zeevaart, THE JOURNAL OF BIOLOGICAL CHEMISTRY, Vol. 276, No. 27, Issue of July 6, pp. 25208–25211, 2001, "Characterization of a Novel Carotenoid Cleavage Dioxygenase from Plants".
  • CAS

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