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Entry
CA00060                                                            

Classification
Carotenoid Name
Phytoene;
(15Z)-Phytoene;
15Z-Phytoene
IUPAC name (15Z)-7,8,11,12,7',8',11',12'-Octahydro-psi,psi-carotene
Formula
C40H64
Molecular Weight 
544.912 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity (Ref.414).
  • Number of
    conjugated double bonds 
    3
    Number of
    conjugated multiple bonds 
    3
    Isomers 
  • Cis/trans isomer: CA00061
  • InChI
    InChI=1S/C40H64/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/h11-12,19-22,27-30H,13-18,23-26,31-32H2,1-10H3/b12-11-,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
    InChIKey
    YVLPJIGOMTXXLP-BHLJUDRVSA-N
    Canonical SMILES
    C/C(=C\C=C/C=C(/CC/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
    14.754
    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
    Rhodobacter capsulatus (Ref.607) - Alphaproteobacteria: photosynthetic purple nonsulfur bacterium
    Thermus thermophilus (Ref.435) - Deinococcus-Thermus: Thermophilic bacterium
    Halobacterium cutirubrum (Ref.331) - Archaea: Euryarchaeota
    Scenedesmus acutus (Ref.50) - Green alga: Scenedesmaceae
    Rhodotorula minuta (Ref.356) - Fungi: red yeast
    Lycopersicon esculentum (Ref.214) - Land plant: Solanaceae: tomato
    Citrus sinensis L. Osbeck (Ref.373) - Land plant: orange
    Homo sapiens (Ref.407) - Human
    References
  • Ref.607 : Glenn E. Bartley and PabloA. Scolnik (1989), The Journal of Biological Chemistry, vol.264, No.22, Issu of August 5, pp.13109-13113, “Carotenoid Biosynthesis inPhotosynthetic Bacteria”.
  • Ref.435 : Yokoyama A, Shizuri Y, Hoshino T, Sandmann G., Arch Microbiol. 1996 May 22;165(5):342-5., "Thermocryptoxanthins: novel intermediates in the carotenoid biosynthetic pathway of Thermus thermophilus".
  • 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.50 : M. Albrecht, G. Sandmann, D. Musker, and G. Britton, J. Agric. Food Chem. 1991, 38, 566-569, "Identification of Epoxy and Hydroxyphytoene from Norflurazon-Treated Scenedesmus".
  • Ref.356 : Tada, Mikiro; Shiroishi, Masahide; Hasegawa, Kiyozo; Suzuki, Tetsuya; Iwai, Kazuo, Plant and Cell Physiology (1982), 23(4), 607-14., "Mechanism of photoregulated carotenogenesis in Rhodotorula minuta.  IV.  Effect of light on the production of ergosterol and phytoene and on the composition of carotenoid pigments".
  • Ref.214 : Ebenezer, Warren J.; Pattenden, Gerald, Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999) (1993), (16), 1869-73., "cis-Stereoisomers of β-carotene and its congeners in the alga Dunaliella bardawil, and their biogenetic interrelationships".
  • 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.407 : Wilhelm Stahl and Helmut Sies, 2012 American Society for Nutrition, "β-Carotene and other carotenoids in protection from sunlight".
  • Ref.414 : Nishino H, Murakosh M, Ii T, Takemura M, Kuchide M, Kanazawa M, Mou XY, Wada S, Masuda M, Ohsaka Y, Yogosawa S, Satomi Y, Jinno K., Cancer Metastasis Rev. 2002;21(3-4):257-64., "Carotenoids in cancer chemoprevention.".
  • CAS
    13920-14-4
    Links to other DB
    KNApSAcK: C00000905
    LipidBank: VCA1001
    ProCarDB: C1754

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