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Entry
CA01017                                                            

Classification
Carotenoid Name
Annuionone F
IUPAC name (5R,6S,7E)-9-Apo-6,916-trihydroxy-5,6-dihydro-beta-caroten-3-one
Formula
C13H22O3
Molecular Weight 
226.306 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical (Ref.401).
  • Potential use as natural herbicide template (Ref.401).
  • Number of
    conjugated double bonds 
    0
    Number of
    conjugated multiple bonds 
    0
    Isomers 
  • Constitutional isomer: CA01023, CA01016, CA01113, CA01114, CA00806
  • InChI
    InChI=1S/C13H22O4/c1-9-6-11(16)7-12(3,8-14)13(9,17)5-4-10(2)15/h4-5,9-10,14-15,17H,6-8H2,1-3H3/b5-4+/t9-,10-,12-,13-/m1/s1
    InChIKey
    RLKZNMMKYFJAPM-UVJNOFBYSA-N
    Canonical SMILES
    OC[C@@]1(C)CC(=O)C[C@H]([C@]1(O)/C=C/[C@H](O)C)C
    XLogP
    0.135
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    0
    Complexity of molecule
    0.154
    Number of heavy atoms
    17
    TPSA
    (Topological Polar Surface Area) 
    77.760 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
    809281-51-4
    Links to other DB

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