2.0 2012-07-30 14:54:37 -0600 2019-04-18 09:58:58 -0600 ECMDB21099 M2MDB001508 (2R,4S)-2-Methyl-2,4-dihydroxydihydrofuran-3-one (2r,4s)-2-methyl-2,4-dihydroxydihydrofuran-3-one belongs to the class of Furanones. These are compounds containing a furan ring bearin a ketone group. (inferred from compound structure) (S)-DHMF pro-AI-2 (vibrio) C5H8O4 132.1146 132.042258744 (2R,4S)-2,4-dihydroxy-2-methyloxolan-3-one (2R,4S)-2,4-dihydroxy-2-methyloxolan-3-one 869748-29-8 C[C@]1(O)OC[C@H](O)C1=O InChI=1S/C5H8O4/c1-5(8)4(7)3(6)2-9-5/h3,6,8H,2H2,1H3/t3-,5-/m0/s1 CCVJVKWZZMMBHB-UCORVYFPSA-N Cytosol logp -1.35 ALOGPS logs 0.84 ALOGPS solubility 9.22e+02 g/l ALOGPS logp -0.66 ChemAxon pka_strongest_acidic 10.46 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (2R,4S)-2,4-dihydroxy-2-methyloxolan-3-one ChemAxon average_mass 132.1146 ChemAxon mono_mass 132.042258744 ChemAxon smiles C[C@]1(O)OC[C@H](O)C1=O ChemAxon formula C5H8O4 ChemAxon inchi InChI=1S/C5H8O4/c1-5(8)4(7)3(6)2-9-5/h3,6,8H,2H2,1H3/t3-,5-/m0/s1 ChemAxon inchikey CCVJVKWZZMMBHB-UCORVYFPSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 28.33 ChemAxon polarizability 11.76 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Quorum Sensing Bacterial Autoinducer 2 (AI-2) mediates the quorum sensing 2 system. AI-2 is catalyzed by the luxS enzyme. This enzyme is found in E.coli and S.typhimurium. In E. coli and most pathogenic bacteria that form AI-2 are spontaneous transformations that include cyclization to (2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one and hydration to the final autoinducer (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran. This product is released from the cell through the AI-2 transporter (tqsA). As the level of AI-2 increases, other cells detect it and import it through the autoinducer-2 ABC transporter (lsrACDB). AI-2 is then degraded in the cells by phosphorylating the AI-2 which is then isomerized to P-HPD which follows by the transfer of and acetyl group to coenzyme A and releases dihydroxyacetone phosphate PW000836 Signaling 10240835 Water + (2R,4S)-2-Methyl-2,4-dihydroxydihydrofuran-3-one > (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran RXN-10017 4,5-Dihydroxy-2,3-pentanedione > (2R,4S)-2-Methyl-2,4-dihydroxydihydrofuran-3-one RXN-10015