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Entry
CA01021                                                            

Classification
Carotenoid Name
Annuionone C
IUPAC name (5S,6S)-9-Apo-9-hydroxy-5,6-epoxy-5,6-dihydro-beta-caroten-3-one
Formula
C13H20O3
Molecular Weight 
224.29 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - stimulates the root growth of barely (Hordeum vulgare) (Ref.401).
  • Potential use as natural herbicide template (Ref.401).
  • Number of
    conjugated double bonds 
    0
    Number of
    conjugated multiple bonds 
    0
    Isomers 
    InChI
    InChI=1S/C13H20O3/c1-9(14)5-6-13-11(2,3)7-10(15)8-12(13,4)16-13/h5-6,9,14H,7-8H2,1-4H3/b6-5+/t9?,12-,13+/m0/s1
    InChIKey
    DZVNWYFIADDOQC-DAUJICFESA-N
    Canonical SMILES
    CC(/C=C/[C@@]12O[C@@]2(C)CC(=O)CC1(C)C)O
    XLogP
    0.946
    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
    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.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
    211183-74-3
    Links to other DB

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