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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   
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
    InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19-,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1
    InChIKey
    SZCBXWMUOPQSOX-NLNQYMAJSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(\C=C\[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C
    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
    Source organisms
    Pittosporum tobira (Ref.310) - Land plant
    Malus domestica (Ref.492) - Land plant: Rosaceae: apple peel extract
    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.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.".
  • CAS
    26927-07-1
    Links to other DB
    KEGG COMPOUND: C13433

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