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Entry
CA01154                                                            

Classification
Carotenoid Name
Sorgolactone;
strigolactone
IUPAC name (3E,3aR,8S,8bS)-8-methyl-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,5,6,7,8,8b-hexahydro-3aH-indeno[1,2-b]furan-2-one
Formula
C18H20O5
Molecular Weight 
316.34 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • An allelochemical - plant 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/C18H20O5/c1-9-4-3-5-11-7-12-13(18(20)23-16(12)15(9)11)8-21-14-6-10(2)17(19)22-14/h6,8-9,12,14,16H,3-5,7H2,1-2H3/b13-8+/t9-,12+,14+,16-/m0/s1
    InChIKey
    KHSREFIWULNDAB-YCUBLIQYSA-N
    Canonical SMILES
    O=C1O[C@H]2[C@@H](/C/1=C\O[C@@H]1OC(=O)C(=C1)C)CC1=C2[C@@H](C)CCC1
    XLogP
    2.363
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    5
    LipinskiFailures
    0
    Complexity of molecule
    0.442
    Number of heavy atoms
    23
    TPSA
    (Topological Polar Surface Area) 
    61.830 Å2
    Source organisms
    Striga spp. (Ref.617) - Land plant: witchweeds, Striga Lour.
    Orobanche spp. (Ref.617) - Land plant: holoparasite
    Phelipanche spp. (Ref.617) - Land plant: Phelipanche Pomel
    Arbuscular mycorrhizal (Ref.594) - Fungi: mycorrhizal fungus
    References
  • Ref.617 : Xiaonan X., Yoneyama K., Kusumoto D., Yamada Y., Takeuchi Y., Sugimoto Y., Yoneyama K., Sorgomol, germination stimulant for root parasitic plants, produced by Sorghum bicolor., Tetrahedron Letters 49 (2008) pp. 2066–2068.
  • 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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