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Entry
CA00312                                                            

Classification
Carotenoid Name
(13Z)-β-Carotene;
13-cis-β-Carotene;
Neo-β-carotene;
Neo-β-carotene B;
13-cis-beta-Carotene;
Neo-beta-carotene;
Neo-beta-carotene B
IUPAC name (13Z)-beta,beta-Carotene
Formula
C40H56
Molecular Weight 
536.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Provitamin A activity - 10% of that of all-trans-β-carotene (Ref.465, Ref.467).
  • Number of
    conjugated double bonds 
    11
    Number of
    conjugated multiple bonds 
    11
    Isomers 
  • Constitutional isomer: CA01132
  • Cis/trans isomer: CA00309, CA00311, CA00310
  • InChI
    InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17-,32-18+,33-21+,34-22+
    InChIKey
    OENHQHLEOONYIE-MZMZTKINSA-N
    Canonical SMILES
    C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C
    XLogP
    14.734
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    1
    Complexity of molecule
    0.312
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Halobacterium cutirubrum (Ref.331) - Archaea: Euryarchaeota
    Synechococcus vulcanus (Ref.197) - Cyanobacteria: hot spring alga
    Passiflora edulis (Ref.129) - Land plant: yellow passion fruit
    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.197 : Grazyna E. Bialek-Bylka, Ritsuko Fujii, Chun-Hai Chen, Hirozo Oh-oka, Akihisa Kamiesu5, Kazuhiko Satoh, Hiroyuki Koike & Yasushi Koyama, Photosynthesis Research 58: 135–142, 1998., "15-Cis-carotenoids found in the reaction center of a green sulfur bacterium Chlorobium tepidum and in the Photosystem I reaction center of a cyanobacterium Synechococcus vulcanus".
  • 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.465 : AKIHIKO NAGAO, AND JAMES ALLEN OLSON, FASEB J. 1994 Sep;8(12):968-73., PMID: 8088462, "Enzymatic formation of 9-cis, 13-cis, and all-trans retinals from isomers of beta-carotene.".
  • Ref.467 : Abdulkerim Eroglu and Earl H. Harrison, Journal of Lipid Research Volume 54, 2013, "Carotenoid metabolism in mammals, including man: formation, occurrence, and function of apocarotenoids".
  • CAS
    6811-73-0
    Links to other DB
    KNApSAcK: C00023249
    ProCarDB: C1757

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