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Entry
CA01020                                                            

Classification
Carotenoid Name
Annuionone B
IUPAC name 9-Apo-17,5-epoxy-5,6-dihydro-beta-caroten-3,9-dione
Formula
C13H18O3
Molecular Weight 
222.274 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - stimulates the root growth of garden cress (Lepidium sativum) (Ref.401).
  • 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 
    InChI
    InChI=1S/C13H18O3/c1-9(14)4-5-11-12(2)6-10(15)7-13(11,3)16-8-12/h4-5,11H,6-8H2,1-3H3/b5-4+/t11-,12-,13-/m1/s1
    InChIKey
    LYMNQFZEIGCRGT-GDNMSKEOSA-N
    Canonical SMILES
    CC(=O)/C=C/[C@@H]1[C@]2(C)CO[C@@]1(C)CC(=O)C2
    XLogP
    0.593
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.235
    Number of heavy atoms
    16
    TPSA
    (Topological Polar Surface Area) 
    43.370 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
    211183-73-2
    Links to other DB

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