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Entry
CA01151                                                            

Classification
Carotenoid Name
5-Deoxystrigol;
strigolactone
IUPAC name (3E,3aR,8bS)-8,8-dimethyl-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-3a,4,5,6,7,8b-hexahydroindeno[1,2-b]furan-2-one
Formula
C19H22O5
Molecular Weight 
330.366 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - plant branching factor, one of the major germination stimulants produced by gramineous plants such as maize, pearl millet, and sorghum after the end of the branching factor (Ref.594).
  • Number of
    conjugated double bonds 
    2 including one ketone and 2 including one ketone (4 in total)
    Number of
    conjugated multiple bonds 
    2 including one ketone and 2 including one ketone (4 in total)
    Isomers 
    InChI
    InChI=1S/C19H22O5/c1-10-7-14(23-17(10)20)22-9-13-12-8-11-5-4-6-19(2,3)15(11)16(12)24-18(13)21/h7,9,12,14,16H,4-6,8H2,1-3H3/b13-9+/t12-,14-,16+/m1/s1
    InChIKey
    QXTUQXRFEBHUBA-DYLOANJQSA-N
    Canonical SMILES
    O=C1O[C@H]2[C@@H](/C/1=C\O[C@@H]1OC(=O)C(=C1)C)CC1=C2C(C)(C)CCC1
    XLogP
    2.775
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    0
    Complexity of molecule
    0.413
    Number of heavy atoms
    24
    TPSA
    (Topological Polar Surface Area) 
    61.830 Å2
    Source organisms
    Arbuscular mycorrhizal (Ref.594) - Fungi: mycorrhizal fungus
    References
  • Ref.594 : Kohki AKIYAMA, Bioscience, Biotechnology, and Biochemistry, 71:6, 1405-1414, DOI: 10.1271/bbb.70023, "Chemical Identification and Functional Analysis of Apocarotenoids Involved in the Development of Arbuscular Mycorrhizal Symbiosis".
  • CAS

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