Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA01161   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
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   
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
    InChI=1S/C20H26O5/c1-13-7-6-10-20(3,4)16(13)9-8-15(19(22)23-5)12-24-17-11-14(2)18(21)25-17/h8-9,11-12,17H,6-7,10H2,1-5H3/b9-8+,15-12+
    InChIKey
    CKPATFHQOSFGEL-BRBUPDJYSA-N
    Canonical SMILES
    COC(=O)/C(=C/OC1OC(=O)C(=C1)C)/C=C/C1=C(C)CCCC1(C)C
    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
    Source organisms
    Arabidopsis sp. (Ref.619) - 
    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

       Search other references with Google Scholar