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Entry
CA00870                                                            

Classification
Carotenoid Name
(6S,7E,9E,11E)-3-Oxo-13-apo-α-caroten-13-one;
3-oxo-13-Apo-ε-caroten-13-one;
3-oxo-13-Apo-epsilon-caroten-13-one;
(6S)-3-oxo-6-hydroxy-13-apo-α-caroten-13-one;
(6S)-3-oxo-6-hydroxy-13-apo-alpha-caroten-13-one
IUPAC name (6S,7E,9E,11E)-3-oxo-13-apo-6-hydroxy-epsilon-caroten-13-one
Formula
C18H24O3
Molecular Weight 
288.372 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical (Ref.401).
  • Inhibites growth of germination of lettuce (Ref.401).
  • Number of
    conjugated double bonds 
    4 and 2 including two ketones (6 in total)
    Number of
    conjugated multiple bonds 
    4 and 2 including two ketones (6 in total)
    Isomers 
  • Constitutional isomer: CA01198
  • InChI
    InChI=1S/C18H24O3/c1-13(7-6-8-15(3)19)9-10-18(21)14(2)11-16(20)12-17(18,4)5/h6-11,21H,12H2,1-5H3/b8-6+,10-9+,13-7+/t18-/m1/s1
    InChIKey
    MIYVERRWVRMENF-YPNYGIKRSA-N
    Canonical SMILES
    C/C(=C\C=C\C(=O)C)/C=C/[C@@]1(O)C(=CC(=O)CC1(C)C)C
    XLogP
    1.834
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.133
    Number of heavy atoms
    21
    TPSA
    (Topological Polar Surface Area) 
    54.370 Å2
    Source organisms
    Chenopodium album (Ref.167) - Land plant: white goosefoot, lamb's-quarters
    References
  • 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
    761409-25-0
    Links to other DB

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