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Entry
CA01018                                                            

Classification
Carotenoid Name
Annuionone G
IUPAC name (3S,5R,6R)-9-Apo-6,7-didehydro-5,6-dihydro-beta-caroten-3,5,9-triol
Formula
C13H22O4
Molecular Weight 
242.306 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: CA01116
  • InChI
    InChI=1S/C13H22O3/c1-9(14)5-6-11-12(2,3)7-10(15)8-13(11,4)16/h5,9-10,14-16H,7-8H2,1-4H3/t6-,9?,10-,13+/m0/s1
    InChIKey
    OWFGLXIJMKELAW-NSJRHIQESA-N
    Canonical SMILES
    CC(C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)O
    XLogP
    2.305
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.158
    Number of heavy atoms
    16
    TPSA
    (Topological Polar Surface Area) 
    60.690 Å2
    Source organisms
    Helianthus annuus (Ref.400) - Land plant: sunflower
    Chenopodium album (Ref.167) - Land plant: white goosefoot, lamb's-quarters
    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.167 : Della Greca, Marina; Di Marino, Cinzia; Zarrelli, Armando; D'Abrosca, Brigida, Journal of Natural Products, Volume67, Issue9, Pages1492-1495, Journal, 2004, CODEN:JNPRDF ISSN:0163-3864 DOI:10.1021/np049857q, "Isolation and phytotoxicity of apocarotenoids from Chenopodium album".
  • 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
    809281-50-3
    Links to other DB

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