Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00869   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00869                                                            

Classification
Carotenoid Name
3-Hydroxy-13-apo-α-caroten-13-one;
3-Hydroxy-13-apo-alpha-caroten-13-one
IUPAC name (3R,6R,7E,11E)-3-Hydroxy-13-apo-epsilon-caroten-13-one
Formula
C18H26O2
Molecular Weight 
274.388 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 including one ketone (4 in total)
    Number of
    conjugated multiple bonds 
    4 including one ketone (4 in total)
    Isomers 
  • Constitutional isomer: CA01003
  • InChI
    InChI=1S/C18H26O2/c1-13(7-6-8-15(3)19)9-10-17-14(2)11-16(20)12-18(17,4)5/h6-11,16-17,20H,12H2,1-5H3/b8-6+,10-9+,13-7+/t16-,17-/m0/s1
    InChIKey
    VFISUJDCZMSIKT-QNPHLTMISA-N
    Canonical SMILES
    C/C(=C\C=C\C(=O)C)/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C
    XLogP
    4.064
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    0
    Complexity of molecule
    0.130
    Number of heavy atoms
    20
    TPSA
    (Topological Polar Surface Area) 
    37.300 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
    761409-24-9
    Links to other DB

       Search other references with Google Scholar