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Entry
CA01161                                                            
Classification
Carotenoid Name
Methyl carlactonoate;
MeCLA
IUPAC name methyl (E,2Z)-6,6-dimethyl-2-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-5-propan-2-ylideneoct-3-enoate;
10-apo-beta-caroten-19-oic acid-methyl-10-(hydroxy-methyl-furanone) (defined by Carotenoids DB)
Formula
C20H26O5
Molecular Weight 
346.408 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - inhibiting shoot branching in Arabidopsis (Ref.619).
    • Number of
    conjugated double bonds 
    4 including one carboxylic acid and 2 including one ketone (6 in total)
    Number of
    conjugated multiple bonds 
    4 including one carboxylic acid and 2 including one ketone (6 in total)
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    4.856
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    0
    Complexity of molecule
    0.314
    Number of heavy atoms
    25
    TPSA
    (Topological Polar Surface Area) 
    61.830 Å2
    Reaction
  • Product: CR00325
    • Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Arabidopsis sp. (Ref.619) -  (Streptophyta - Brassicaceae)
    References
  • Ref.619: Abe S., Sado A., Tanaka K., Kisugi T., Asami K., Ota S., Kim H. II., Yoneyama K., Xiaonan Xie, Ohnishi T., Seto Y., Yamaguchi S., Akiyama K., Yoneyama K., Nomura T. (2014), Carlactone is converted to carlactonoic acid by MAX1 in Arabidopsis and its methyl ester can directly interact with AtD14 in vitro, PNAS, December 16, 2014, vol. 111, no. 50, pp.18084–18089, www.pnas.org/cgi/doi/10.1073/pnas.1410801111.
    • CAS

    Links to other DB

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