Coronatine

Coronatine

Names
IUPAC name (1S,2S)-2-Ethyl-1-({[(3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]carbonyl}amino)cyclopropanecarboxylic acid
Identifiers
CAS Number	62251-96-1
ChemSpider	82784
Jmol 3D model	Interactive image
PubChem	91681
InChI InChI=1S/C18H25NO4/c1-3-10-7-13-12(5-6-15(13)20)14(8-10)16(21)19-18(17(22)23)9-11(18)4-2/h8,10-13H,3-7,9H2,1-2H3,(H,19,21)(H,22,23)/t10-,11+,12+,13+,18+/m1/s1 Key: FMGBNISRFNDECK-CZSBRECXSA-N InChI=1/C18H25NO4/c1-3-10-7-13-12(5-6-15(13)20)14(8-10)16(21)19-18(17(22)23)9-11(18)4-2/h8,10-13H,3-7,9H2,1-2H3,(H,19,21)(H,22,23)/t10-,11+,12+,13+,18+/m1/s1 Key: FMGBNISRFNDECK-CZSBRECXBX
SMILES O=C(O)[C@@]3(NC(=O)/C1=C/[C@@H](C[C@@H]2C(=O)CC[C@H]12)CC)[C@@H](CC)C3
Properties
Chemical formula	C18H25NO4
Molar mass	319.40 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Coronatine (COR) is a toxin produced by the bacterium Pseudomonas syringae. It is involved in causing stomata to re-open after they close in response to pathogen-associated molecular patterns, as well as interfering with the responses mediated by salicylic acid after the infection has begun. It consists of coronafacic acid (CFA), which is an analog of methyl jasmonic acid (MeJA), and coronamic acid (CMA), joined by an amide bond between the acid group of CFA and the amino group of CMA.^[1]

References

1. Melotto, Maeli; Underwood, William; He, Sheng Yang (2008). "Role of Stomata in Plant Innate Immunity and Foliar Bacterial Diseases". Annual Review of Phytopathology 46: 101–22. doi:10.1146/annurev.phyto.121107.104959. PMC 2613263. PMID 18422426.