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Entry
CA00051                                                            

Classification
Carotenoid Name
ζ-Carotene;
zeta-Carotene;
all-trans-zeta-carotene
IUPAC name 7,8,7',8'-Tetrahydro-psi,psi-carotene
Formula
C40H60
Molecular Weight 
542.896 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Non-provitamin A. (Ref.468)
  • Yellow food coloring (Ref.468).
  • Number of
    conjugated double bonds 
    7
    Number of
    conjugated multiple bonds 
    7
    Isomers 
  • Constitutional isomer: CA00049, CA00048, CA00050, CA00195, CA00300, CA00318
  • Cis/trans isomer: CA00065, CA00053, CA00163
  • InChI
    InChI=1S/C40H60/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/h11-12,15-16,19-22,25-30H,13-14,17-18,23-24,31-32H2,1-10H3/b12-11+,25-15+,26-16+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
    InChIKey
    BIWLELKAFXRPDE-WTXAYMOSSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\CC/C=C(/CCC=C(C)C)\C)/C)/C)/C=C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C
    XLogP
    14.670
    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
    Oscillantoria rubescens (Ref.2) - Cyanobacteria: other name is Planktothrix rubescens
    Passiflora edulis (Ref.129) - Land plant: yellow passion fruit
    Citrullus vulgaris (Ref.484) - Land plant: watermelon
    Carica papaya (Ref.566) - Land plant: papaya
    Averrhoa carambola (Ref.281) - Land plant: starfruit
    Ipomoea batatas Lam. (Ref.295) - Land plant: sweet potato
    Calendula officinalis (Ref.430) - Land plant: common marigold
    Staphylococcus aureus (Ref.540) - Firmicutes - Bacilli
    References
  • Ref.2 : D. Chamovitz, I. Peeker, and J. Hirtschberg, Plant Molecular Biology 16: 967-974, 1991 "The molecular basis of resistance to the herbicide norflurazon".
  • Ref.129 : da Silva, Sandra Regina; Mercadante, Adriana Z., Ciencia e Tecnologia de Alimentos (Campinas, Brazil) (2002), 22(3), 254-258., "Carotenoid composition of fresh yellow passion fruit (Passiflora edulis flavicarpa)".
  • 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.566 : U Gamage Chandrika, Errol R Jansz, SMD Nalinie Wickramasinghe and Narada D Warnasuriya, J Sci Food Agric 83:1279–1282 (online: 2003), DOI: 10.1002/jsfa.1533, "Carotenoids in yellow- and red-fleshed papaya (Carica papaya L)".
  • 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.295 : Ligia B. Almeida, Marilene V.C. Penteado, Journal of Food Composition and Analysis, Volume 1, Issue 4, November 1988, Pages 341–352, "Carotenoids and pro-vitamin A value of white fleshed Brazilian sweet potatoes (Ipomoea batatas Lam.)".
  • 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.540 : Benjamin N. Mijts, Pyung Cheon Lee, Claudia Schmidt-Dannert, Chemistry & Biology, Volume 12, Issue 4, April 2005, Pages 453–460, "Identification of a Carotenoid Oxygenase Synthesizing Acyclic Xanthophylls: Combinatorial Biosynthesis and Directed Evolution".
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • CAS
    72746-33-9
    Links to other DB
    KEGG COMPOUND: C05430
    KNApSAcK: C00000934
    LipidBank: VCA1003
    MassBank: CA000164
    ProCarDB: C1723

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