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Entry
CA00429                                                            

Classification
Carotenoid Name
Dinoxanthin
IUPAC name (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-6',7'-didehydro-5,6,5',6'-tetrahydro-beta,beta-carotene-3,5'-diol
Formula
C42H58O5
Molecular Weight 
642.884 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
  • Constitutional isomer: CA00358, CA00999, CA00765
  • InChI
    InChI=1S/C42H58O5/c1-30(18-14-20-32(3)22-23-37-38(6,7)28-36(46-34(5)43)29-40(37,10)45)16-12-13-17-31(2)19-15-21-33(4)24-25-42-39(8,9)26-35(44)27-41(42,11)47-42/h12-22,24-25,35-36,44-45H,26-29H2,1-11H3/b13-12+,18-14+,19-15+,25-24+,30-16+,31-17+,32-20+,33-21+/t23-,35-,36-,40+,41+,42-/m0/s1
    InChIKey
    PVNVIBOWBAPFOE-GYMZYDTCSA-N
    Canonical SMILES
    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=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)\C
    XLogP
    11.059
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    2
    Complexity of molecule
    0.295
    Number of heavy atoms
    47
    TPSA
    (Topological Polar Surface Area) 
    79.290 Å2
    Source organisms
    Pavlova lutheri (Ref.31) - Alga: Haptophyte
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate
    Gymnodinum splendens (Ref.33) - Alga: Dinoflagellate
    Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate
    Gonyostomum semen (Ref.35) - Alga: Raphidophyceae
    Vacuolaria virescens (Ref.35) - Alga: Raphidophyceae
    References
  • Ref.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • Ref.33 : J. E. Joansen, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1974, Vol.13 pp.2261-2271, "Carotenoids of the Dinophyceae".
  • Ref.34 : R. Frassanito G. Flaim, I. Mancini, G. Guella, Biochemical Systematics and Ecology 34 (2006) pp.843-853, "High production of unexpected carotenoids in Dinophyceae. Astaxanthin esters from freshwater dinoflagellate Tovellia sanguinea".
  • Ref.35 : A.Fiksdahl, N. Withers, R. R. L. Guillard, and S. Liaaen-Jensen, Comp. Biochem. Physiol. Vol. 78B, No. 1, pp. 265-271, 1984, "Carotenoids of the Raphidophyceae - a chemosystematic contribution ".
  • CAS
    54369-12-9
    Links to other DB
    KNApSAcK: C00022944

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