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Entry
CA00057                                                            

Classification
Carotenoid Name
Phytofluene;
(15Z)-Phytofluene;
15-cis-Phytofluene;
Hexahydrolycopene
IUPAC name (15Z)-7,8,11,12,7',8'-Hexahydro-psi,psi-carotene
Formula
C40H62
Molecular Weight 
542.896 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity - more active than β-carotene (Ref.491).
  • Number of
    conjugated double bonds 
    5
    Number of
    conjugated multiple bonds 
    5
    Isomers 
  • Cis/trans isomer: CA00059, CA00058
  • InChI
    InChI=1S/C40H62/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15,19-22,25,27-30H,13-14,16-18,23-24,26,31-32H2,1-10H3/b12-11-,25-15+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
    InChIKey
    OVSVTCFNLSGAMM-DGFSHVNOSA-N
    Canonical SMILES
    C/C(=C\C=C/C=C(/C=C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C)/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C
    XLogP
    14.712
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Halobacterium cutirubrum (Ref.331) - Archaea: Euryarchaeota
    Rhodopseudomonas viridis (Ref.212) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Averrhoa carambola (Ref.281) - Land plant: starfruit
    Citrus sinensis L. Osbeck (Ref.373) - Land plant: orange
    Citrullus vulgaris (Ref.484) - Land plant: watermelon
    Calendula officinalis (Ref.430) - Land plant: common marigold
    Homo sapiens (Ref.407) - Human
    References
  • Ref.331 : Kushwaha, S. C.; Pugh, E. L.; Kramer, J. K. G.; Kates, M., Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1972), 260(3), 492-506., "Isolation and identification of dehydrosqualene and C40 carotenoid pigments in Halobacterium cutirubrum cutirubrum".
  • Ref.212 : Malhotra, H. C.; Britton, Geoffrey; Goodwin, Trevor W., Internationale Zeitschrift fuer Vitaminforschung (1970), 40(3), 315-22. "Novel series of 1,2-dihydrocarotenoids".
  • Ref.281 : Jeana Gross, Raphael Ikan, Gert Eckhardt, Phytochemistry, Volume 22, Issue 6, 1983, Pages 1479-1481, "Carotenoids of the fruit of Averrhoa carambola".
  • Ref.373 : Kudritskaya, S. E.; Fishman, G. M.; Zagorodskaya, L. M., Subtropicheskie Kul'tury (1977), (5-6), 154-8., "Identification of orange peel (Citrus sinensis Osb.) carotenoids".
  • Ref.484 : Wen’en Zhao, Pin Lv, Huihui Gu, Agricultural Sciences Vol.4, No.7A, 13-20 (2013), http://dx.doi.org/10.4236/as.2013.47A003, "Studies on carotenoids in watermelon flesh".
  • Ref.430 : T. W. GOODWIN, Biochem J. 1954 Sep;58(1):90-4., "Studies in carotenogenesis. 13. The carotenoids of the flower petals of Calendula officinalis.".
  • Ref.407 : Wilhelm Stahl and Helmut Sies, 2012 American Society for Nutrition, "β-Carotene and other carotenoids in protection from sunlight".
  • Ref.491 : Tsushima M, Maoka T, Katsuyama M, Kozuka M, Matsuno T, Tokuda H, Nishino H, Iwashima A., Biol Pharm Bull. 1995 Feb;18(2):227-33., PMID: 7742789, "Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters.".
  • CAS
    27664-65-9
    Links to other DB
    KNApSAcK: C00000913
    LipidBank: VCA1002
    MassBank: CA000158
    ProCarDB: C1024

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