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Entry
CA00805                                                            
Classification
Carotenoid Name
Blumenol A;
Vomifoliol;
(+)-Vomifoliol
IUPAC name (6R,9RS)-6,9-dihydroxy-9-apo-epsilonn-caroten-3-one
Formula
C13H20O3
Molecular Weight 
224.29 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical (Ref.469). Cytotoxic against human solid tumor cells, but not significantly potent (Ref.654). Inhibitory effects on radicle growth in lettuce and weeds (Ref.655).
    • Number of
    conjugated double bonds 
    2 including one ketone (2 in total)
    Number of
    conjugated multiple bonds 
    2 including one ketone (2 in total)
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    0.644
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.167
    Number of heavy atoms
    16
    TPSA
    (Topological Polar Surface Area) 
    57.530 Å2
    Reaction
    Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Solanum lyratum (Ref.394) - Land plant: Solanaceae: Inedible plant for humans (Streptophyta - Solanaceae)
    Podocarpus blumei (Ref.186) - Land plant (Streptophyta - Pinidae)
    Chrysanthemum indicum (Ref.399) - Land plant: chrysanthemum (Streptophyta - Asteraceae)
    Tectona grandis (Ref.469) - Land plant: Teak (Streptophyta - Lauraceae)
    References
  • Ref.186: M. N. Galbraith and D. H. S. Horn, J. Chem. Soc., Chem. Commun., 1972, 113-114, "Structures of the natural products blumenols A, B, and C".
  • Ref.394: Yue, Xi-dian; Yao, Fang; Zhang, Lei; Li, Gui-sheng; Dai, Sheng-jun, Zhongguo Zhongyao Zazhi (2014), 39(3), 453-456., "Sesquiterpenoids from Solanum lyratum".
  • Ref.399: Feng, Ziming; Yang, Yanan; Jiang, Jianshuang; Zhang, Peicheng, Zhongguo Zhongyao Zazhi (2010), 35(24), 3302-3305., "Chemical constituents from flowers of Chrysanthemum indicum".
  • Ref.469: Francisco A. Macíasa, Rodney Lacreta, Rosa M. Varelaa, Clara Nogueirasb, Jose M.G. Molinillo, Phytochemistry, Volume 69, Issue 15, November 2008, Pages 2708–2715, "Bioactive apocarotenoids from Tectona grandis".
  • Ref.654: Xiaoxi Liu , Feifei Tian , Hong-Bing Zhang , Elsa Pilarinou, and Jerry L. McLaughlin, Natural Product Letters Volume 14, 1999 - Issue 1, Pages 77-81, "Biologically Active Blumenol A from the Leaves of Annona Glabra", https://doi.org/10.1080/10575639908045437.
  • Ref.655: Manoel Albuquerque, Roseane Santos, Liziane Lima, Péricles Melo Filho, Rejane Nogueira, Claudio Câmara, Ramos, Agronomy for Sustainable Development, April 2011, Volume 31, Issue 2, pp 379–395, "Allelopathy, an alternative tool to improve cropping systems. A review", https://doi.org/10.1051/agro/2010031.
    • CAS
    23526-45-6
    Links to other DB

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