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Entry
CA00976                                                            

Classification
Carotenoid Name
(9Z)-Violaxanthin;
9-cis-Violaxanthin
IUPAC name (9Z,3S,5R,6S,3'S,5'R,6'S)-5,6:5',6'-Diepoxy-tetrahydro-beta,beta-carotene-3,3'-diol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Effective MDR modulator (Ref.493, Ref.582).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
  • Cis/trans isomer: CA00416
  • Constitutional isomer: CA00748
  • InChI

    InChIKey

    Canonical SMILES

    XLogP
    8.964
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    65.520 Å2
    Reaction
  • Substrate: CR00045,  CR00047,  CR00090,  CR00383,  CR00455
  • Product: CR00358
  • Pathway
    Major carotenoid information
    Major carotenoid in land plants (Ref.732).
    Minor carotenoid information

    Source organisms
    Arabidopsis thaliana (Ref.762) - Land plant: thale-cress, a model organism (Streptophyta - Brassicaceae)
    Passiflora edulis (Ref.693) - Land plant: yellow passion fruit (Streptophyta - Passifloraceae)
    Pittosporum tobira (Ref.310) - Land plant (Streptophyta - Pittosporaceae)
    Malus domestica (Ref.492) - Land plant: Rosaceae: peel and flesh of apple fruits (Streptophyta - Rosaceae)
    References
  • Ref.310: Fujiwara, Yasuhiro; Maruwaka, Hisashi; Toki, Fujio; Hashimoto, Keiji; Maoka, Takashi, Chemical & Pharmaceutical Bulletin (2001), 49(8), 985-987., "Structure of three new carotenoids with a 3-methoxy-5-keto-5,6-seco-4,6-cyclo-β end group from the seeds of Pittosporum tobira".
  • Ref.492: Péter Molnár, József Deli, Toru Tanaka,Yoshiyuki Kann, Satoru Tani, Nóra Gyémánt, Joseph Molnár ,and Masami Kawase, Phytotherapy Research, Volume 24, Issue 5, pages 644–648, May 2010, “Carotenoids with anti-Helicobacter pylori activity from Golden deliciousapple”.
  • Ref.693: M. Yano et al., Food Science and Technology Research, 11(1), pp.13-18, 2005, "Quantitation of Carotenoids in Raw and Processed Fruits in Japan", DOI: https://doi.org/10.3136/fstr.11.13.
  • 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.493: Anne-Laure Gagez, Valérie Thiery, Virginie Pasquet, Jean-Paul Cadoret, and Laurent Picot, Current Bioactive Compounds 2012, 8, 000-000, "Epoxycarotenoids and Cancer. Review".
  • Ref.582: Gyémánt N, Tanaka M, Molnár P, Deli J, Mándoky L, Molnár J., Anticancer Res. 2006 Jan-Feb;26(1A):367-74., PMID: 16475720, "Reversal of multidrug resistance of cancer cells in vitro: modification of drug resistance by selected carotenoids.".
  • Ref.732: S. Takaichia and M. Mochimaru, Cell. Mol. Life Sci. 64 (2007) 2607 – 2619, "Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides", DOI 10.1007/s00018-007-7190-z.
  • CAS
    26927-07-1
    Links to other DB
    KEGG COMPOUND: C13433

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