2.0 2015-09-08 17:50:19 -0600 2015-09-14 16:46:42 -0600 ECMDB24234 M2MDB006351 3-hydroxy-2,4-pentanedione 5-phosphate 3-Hydroxy-2,4-pentanedione 5-phosphate is an intermediate in autoinducer AI-2 degradation pathway in E.coli. It is a substrate for the enzyme 3-hydroxy-2,4-pentadione 5-phosphate thiolase which catalyzes the reaction 3-hydroxy-5-phosphonooxypentane-2,4-dione + coenzyme A -> glycerone phosphate + acetyl-CoA. It is also a product for enzyme phospho-AI-2 isomerase which catalyzes reaction (4S)-4-hydroxy-5-phosphonooxypentane-2,3-dione -> 3-hydroxy-5-phosphonooxypentane-2,4-dione (BioCyc compound: CPD0-2467). 3-Hydroxy-2,4-pentanedione 5-phosphoric acid C5H7O7P 210.079 209.994036723 3-hydroxy-1-(phosphonatooxy)pentane-2,4-dione 3-hydroxy-1-(phosphonatooxy)pentane-2,4-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/h5,8H,2H2,1H3,(H2,9,10,11)/p-2 AKHNGSPNHAFBII-UHFFFAOYSA-L logp -0.90 ALOGPS logs -0.75 ALOGPS solubility 4.39e+01 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 1.17 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 3-hydroxy-1-(phosphonatooxy)pentane-2,4-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/h5,8H,2H2,1H3,(H2,9,10,11)/p-2 ChemAxon inchikey AKHNGSPNHAFBII-UHFFFAOYSA-L ChemAxon polar_surface_area 126.79 ChemAxon refractivity 37.76 ChemAxon polarizability 15.87 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 250088 Specdb::NmrOneD 250089 Specdb::NmrOneD 250090 Specdb::NmrOneD 250091 Specdb::NmrOneD 250092 Specdb::NmrOneD 250093 Specdb::NmrOneD 250094 Specdb::NmrOneD 250095 Specdb::NmrOneD 250096 Specdb::NmrOneD 250097 Specdb::NmrOneD 250098 Specdb::NmrOneD 250099 Specdb::NmrOneD 250100 Specdb::NmrOneD 250101 Specdb::NmrOneD 250102 Specdb::NmrOneD 250103 Specdb::NmrOneD 250104 Specdb::NmrOneD 250105 Specdb::NmrOneD 250106 Specdb::NmrOneD 250107 Specdb::MsMs 29108 Specdb::MsMs 29109 Specdb::MsMs 29110 Specdb::MsMs 35666 Specdb::MsMs 35667 Specdb::MsMs 35668 (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 3-hydroxy-2,4-pentanedione 5-phosphate + Coenzyme A + 3-hydroxy-2,4-pentanedione 5-phosphate > Acetyl-CoA + Dihydroxyacetone phosphate PW_R003073