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Entry
CA00311                                                            
Classification
Carotenoid Name
(9Z)-β-Carotene;
9-cis-β-Carotene;
9-cis-beta-Carotene
IUPAC name (9Z)-beta,beta-Carotene
Formula
C40H56
Molecular Weight 
536.848 g/mol
Structure      Search similar carotenoids

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: CA01131
  • Cis/trans isomer: CA00309, CA00312, CA00310
    • InChI

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00040,  CR00082,  CR00421
  • Product: CR00357,  CR00372
    • Pathway
  • Pathway: CB000079,  CB000085,  CB000086,  CB000129
    • Major carotenoid information

    Minor carotenoid information

    Source organisms
    Synechococcus vulcanus (Ref.197) - Cyanobacteria: hot spring alga (Cyanobacteria - Synechococcaceae)
    Dunaliella bardawil (Ref.214) - Green alga: Dunaliellaceae (Chlorophyta - Dunaliellaceae)
    Arabidopsis thaliana (Ref.762) - Land plant: thale-cress, a model organism (Streptophyta - Brassicaceae)
    Homo sapiens (Ref.425) - Mammal: Human (Chordata - Hominidae)
    References
  • 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.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.762: Kerry L. Taylor, Anika E. Brackenridge, Melane A. Vivier, Anita Oberholster, Journal of Chromatography A, 1121 (2006) 83–91, "High-performance liquid chromatography profiling of the major carotenoids in Arabidopsis thaliana leaf tissue".
  • Ref.425: Wilhelm Stahl, Wolfgang Schwarz, Alfred R. Sundquist, Helmut Sies, Archives of Biochemistry and Biophysics, Volume 294, Issue 1, April 1992, Pages 173–177, "cis-trans isomers of lycopene and β-carotene in human serum and tissues".
  • 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
    13312-52-2
    Links to other DB
    KEGG COMPOUND: C20484
    KNApSAcK: C00023248

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