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Entry
CA01022                                                            

Classification
Carotenoid Name
Annuionone D
IUPAC name (3S,5S,6S)-9-Apo-3-hydroxy-5,6-epoxy-5,6-dihydro-beta-caroten-9-one
Formula
C13H20O3
Molecular Weight 
224.29 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - stimulates the root elongation of onion (Allium cepa), and barely.: Hordeum vulgare (Ref.401, Ref.469).
  • Potential use as natural herbicide template (Ref.401).
  • 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 
  • Constitutional isomer: CA01021, CA01019, CA01012, CA01118, CA01015, CA00805, CA00843
  • Conformer: CA01014
  • InChI
    InChI=1S/C13H20O3/c1-9(14)5-6-13-11(2,3)7-10(15)8-12(13,4)16-13/h5-6,10,15H,7-8H2,1-4H3/b6-5+/t10-,12-,13+/m0/s1
    InChIKey
    VYKLRWGPNUVKNC-HNSJSBKASA-N
    Canonical SMILES
    CC(=O)/C=C/[C@@]12O[C@@]2(C)C[C@H](CC1(C)C)O
    XLogP
    1.187
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.194
    Number of heavy atoms
    16
    TPSA
    (Topological Polar Surface Area) 
    49.830 Å2
    Source organisms
    Helianthus annuus (Ref.400) - Land plant: sunflower
    Tectona grandis (Ref.469) - Land plant: Teak
    References
  • Ref.400 : Macias, Francisco A.; Lopez, Adriana; Varela, Rosa M.; Torres, Ascension; Molinillo, Jose M. G., Phytochemistry (Elsevier) (2004), 65(22), 3057-3063., "Bioactive apocarotenoids annuionones F and G: structural revision of annuionones A, B and E".
  • 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.401 : Luiz Cláudio Almeida Barbosa, Róbson Ricardo Teixeira, Ricardo Marques Montanari, 2009, "PHYTOTOXIC NATURAL PRODUCTS AS MODELS FOR THE DEVELOPMENT OF CROP PROTECTION AGENTS".
  • CAS
    61116-99-2
    Links to other DB

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