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Entry
CA01023                                                            

Classification
Carotenoid Name
Annuionone E
IUPAC name (9S)-9-Apo-9-hydroxy-17,5-epoxy-5,6,7,8-tetrahydro-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: CA01017, CA01016, CA01113, CA01114, CA00806
  • InChI
    InChI=1S/C13H22O3/c1-9(14)4-5-11-12(2)6-10(15)7-13(11,3)16-8-12/h9,11,14H,4-8H2,1-3H3/t9?,11-,12-,13-/m1/s1
    InChIKey
    YLXMIDJRRREVMX-JINIMCQISA-N
    Canonical SMILES
    CC(CC[C@@H]1[C@]2(C)CO[C@@]1(C)CC(=O)C2)O
    XLogP
    1.015
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.211
    Number of heavy atoms
    16
    TPSA
    (Topological Polar Surface Area) 
    46.530 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
    497931-65-4
    Links to other DB

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