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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).
  • 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
    InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10?,13-/m1/s1
    InChIKey
    KPQMCAKZRXOZLB-ZKQKWALRSA-N
    Canonical SMILES
    CC(/C=C/[C@@]1(O)C(=CC(=O)CC1(C)C)C)O
    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
    Source organisms
    Podocarpus blumei (Ref.186) - Land plant
    Solanum lyratum (Ref.394) - Land plant: Solanaceae: Inedible plant for humans
    Chrysanthemum indicum (Ref.399) - Land plant: chrysanthemum
    Tectona grandis (Ref.469) - Land plant: Teak
    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".
  • CAS
    23526-45-6
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