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Substrate Report for: GR24

A commonly used synthetic strigolactone analog invented by Gerald Rosebery. Strigolactones (SL) are butenolide plant hormones with tricyclic lactone, that influence root branching leaf shape and senescence. Karrikins (KAR) are different butenolide molecules produced during wildfires in smoke and deposited on soil surface. They are absorbed by seeds and activate germination. KAI2 and D14 are paralogous alpha/beta hydrolase receptors respectively for KARs and SLs they belong to the RsbQ-like family. KAI2 (KARRIKIN-INSENSITVE-2) and D14 (DWARF14) are both receptors and enzymes. The racemic GR24 has both Karrikin and Strigolactone activities as the stereochemistry at the 2' carbon of the butenolide D-ring is identical to the one of 5-deoxystrigol acts as Stigolactone.The other enantiomer acts preferrencially on KAI2 receptor. (+)-GR24 and (-)2'-epi-GR24 have stereochemistry corresponding to taht of natural canonicla SLs of the strigol-type and orobanchol-type respectivly. (-)-GR24 and (+)2'-epi-GR24 stereochemistry is not encountred in natural SLs


General
Type Strigolactone, Butenolide, Strigolactone receptors ligand, Inden
Chemical_Nomenclature (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one
Canonical SMILES CC1=CC(OC1=O)OC=C2C3CC4=CC=CC=C4C3OC2=O
InChI InChI=1S/C17H14O5/c1-9-6-14(21-16(9)18)20-8-13-12-7-10-4-2-3-5-11(10)15(12)22-17(13)19/h2-6,8,12,14-15H,7H2,1H3/b13-8+
InChIKey XHSDUVBUZOUAOQ-MDWZMJQESA-N XHSDUVBUZOUAOQ-WSTIHDONSA-N XHSDUVBUZOUAOQ-IMBONUEFSA-N
Other name(s) SCHEMBL9983619 ; CHEMBL2447920 ; AC1MI1TT ; (+)-epi-GR-24 ; SCHEMBL13974737 ; ZINC33753817 ; PL021299 ; dGR24ent-5DS ; rac-GR24
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MW|298.29
Formula|C17H14O5
CAS_number|
PubChem|11748521, 3036799, 102518383
UniChem|XHSDUVBUZOUAOQ-MDWZMJQESA-N, XHSDUVBUZOUAOQ-WSTIHDONSA-N, XHSDUVBUZOUAOQ-IMBONUEFSA-N
IUPHAR|
Wikipedia|Strigolactone

Target
Families | GR24 ligand of proteins in family: RsbQ-like, Fungal-D14-Strigolactone-R
Stucture | 4 structures (e.g. : 7K38, 8DVC, 5DJ5... more)
Protein | orysj-Q10QA5, pea-RMS3, arath-AtD14, arath-KAI2.D14L, orysa-q6l556, crypa-CpD14

References:
Search PubMed for references concerning: GR24

6 more
    Title: Desmethyl butenolides are optimal ligands for karrikin receptor proteins
    Yao J, Scaffidi A, Meng Y, Melville KT, Komatsu A, Khosla A, Nelson DC, Kyozuka J, Flematti GR, Waters MT
    Ref: New Phytol, :, 2021 : PubMed

            

    Title: An allelic series at the KARRIKIN INSENSITIVE 2 locus of Arabidopsis thaliana decouples ligand hydrolysis and receptor degradation from downstream signalling
    Yao J, Mashiguchi K, Scaffidi A, Akatsu T, Melville KT, Morita R, Morimoto Y, Smith SM, Seto Y and Waters MT <2 more author(s)>
    Ref: Plant J, 96:75, 2018 : PubMed

            

    Title: The preparation of synthetic analogues of strigol
    Johnson AW, Gowda G, Wassanali A, Knox J, Monaco S, Razawi Z, Roseberry G
    Ref: J Chem Soc Perkin 1, :1734, 1981 : PubMed