2.0 2015-09-08 17:50:19 -0600 2015-09-14 16:46:41 -0600 ECMDB24233 M2MDB006350 (4S)-4-hydroxy-2,3-pentanedione 5-phosphate (4S)-4-Hydroxy-2,3-pentanedione 5-phosphate is an intermediate in autoinducer AI-2 degradation pathway in E.coli. It is a substrate for the enzyme phospho-AI-2 isomerase which catalyzes the reaction (4S)-4-hydroxy-2,3-pentanedione 5-phosphate -> 3-hydroxy-2,4-pentanedione 5-phosphate. It is also a product for enzyme autoinducer-2 kinase which catalyzes reaction autoinducer 2 + ATP -> (4S)-4-hydroxy-2,3-pentanedione 5-phosphate + ADP + H+ (BioCyc compound: CPD-10551). (4S)-4-Hydroxy-2,3-pentanedione 5-phosphoric acid C5H7O7P 210.079 209.994036723 4-hydroxy-5-(phosphonatooxy)pentane-2,3-dione 4-hydroxy-5-(phosphonatooxy)pentane-2,3-dione CC(=O)C(=O)C(O)COP([O-])([O-])=O InChI=1S/C5H9O7P/c1-3(6)5(8)4(7)2-12-13(9,10)11/h4,7H,2H2,1H3,(H2,9,10,11)/p-2 DTZHMTDUIGHESZ-UHFFFAOYSA-L logp -0.93 ALOGPS logs -0.74 ALOGPS solubility 4.51e+01 g/l ALOGPS logp -1 ChemAxon pka_strongest_acidic 1.37 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 4-hydroxy-5-(phosphonatooxy)pentane-2,3-dione ChemAxon average_mass 210.079 ChemAxon mono_mass 209.994036723 ChemAxon smiles CC(=O)C(=O)C(O)COP([O-])([O-])=O ChemAxon formula C5H7O7P ChemAxon inchi InChI=1S/C5H9O7P/c1-3(6)5(8)4(7)2-12-13(9,10)11/h4,7H,2H2,1H3,(H2,9,10,11)/p-2 ChemAxon inchikey DTZHMTDUIGHESZ-UHFFFAOYSA-L ChemAxon polar_surface_area 126.79 ChemAxon refractivity 37.91 ChemAxon polarizability 16.02 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 1 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 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 Specdb::NmrOneD 259608 Specdb::NmrOneD 259609 Specdb::NmrOneD 259610 Specdb::NmrOneD 259611 Specdb::NmrOneD 259612 Specdb::NmrOneD 259613 Specdb::NmrOneD 259614 Specdb::NmrOneD 259615 Specdb::NmrOneD 259616 Specdb::NmrOneD 259617 Specdb::NmrOneD 259618 Specdb::NmrOneD 259619 Specdb::NmrOneD 259620 Specdb::NmrOneD 259621 Specdb::NmrOneD 259622 Specdb::NmrOneD 259623 Specdb::NmrOneD 259624 Specdb::NmrOneD 259625 Specdb::NmrOneD 259626 Specdb::NmrOneD 259627 Specdb::MsMs 25151 Specdb::MsMs 25152 Specdb::MsMs 25153 Specdb::MsMs 31709 Specdb::MsMs 31710 Specdb::MsMs 31711 (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine triphosphate + (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran > Adenosine diphosphate + Hydrogen ion + (4S)-4-hydroxy-2,3-pentanedione 5-phosphate + ADP + (4S)-4-hydroxy-2,3-pentanedione 5-phosphate PW_R003071 (4S)-4-hydroxy-2,3-pentanedione 5-phosphate + (4S)-4-hydroxy-2,3-pentanedione 5-phosphate > 3-hydroxy-2,4-pentanedione 5-phosphate + 3-hydroxy-2,4-pentanedione 5-phosphate PW_R003072