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Entry
CA00841                                                            

Classification
Carotenoid Name
Apo-12'-violaxanthal
IUPAC name (3S,5R,6S)-5,6-Epoxy-3-hydroxy-5,6-dihydro-12'-apo-beta-caroten-12'-al
Formula
C25H34O3
Molecular Weight 
382.522 g/mol
Structure      Search similar carotenoids

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: CA01135
  • Constitutional isomer: CA01090, CA00881
  • 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-LKODNMENSA-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
    Peltigera ponojensis (Ref.237) - Fungi: foliose lichen, commonly known as the dog lichen
    Citrus sinensis (Ref.162) - Land plant: orange
    References
  • Ref.237 : Czeczuga, B.; Beckett, R. P.; Pienaar, R. N., South African Journal of Botany (1988), 54(6), 571-4., "Investigations on carotenoids in lichens.  XVIII.  Carotenoid content in certain lichens from southern Africa".
  • Ref.162 : Pétter Molnár, József Szabolcs, Phytochemistry (1980), Volume 19, Issue 4, Pages 633–637, "β-Citraurin epoxide, a new carotenoid from valencia orange peel".
  • CAS
    62777-81-5
    Links to other DB

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