2.0 2015-06-04 16:14:45 -0600 2015-09-14 16:46:22 -0600 ECMDB23825 M2MDB004543 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate is an intermediate in thiamin diphosphate biosynthesis I in E.coli, where it is a substrate for the enzyme thiamine phosphate synthase which catalyzes the reaction 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate + 4-amino-2-methyl-5-diphosphomethylpyrimidine + 2 H+ -> thiamin phosphate + CO2 + diphosphate. In thiazole biosynthesis I, it is a product for enzyme thiazole synthase which catalyzes reaction 1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + a thiocarboxy-[ThiS-Protein] -> 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate + a ThiS sulfur-carrier protein + 2 H2O. (BioCyc compound: CPD-13575). 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphoric acid C7H10NO6PS 267.19 266.996645218 (2R,5Z)-4-methyl-5-[2-(phosphonooxy)ethylidene]-2,5-dihydro-1,3-thiazole-2-carboxylic acid (2R,5Z)-4-methyl-5-[2-(phosphonooxy)ethylidene]-2H-1,3-thiazole-2-carboxylic acid CC1=N[C@H](S\C1=C/COP(O)(O)=O)C(O)=O InChI=1S/C7H10NO6PS/c1-4-5(2-3-14-15(11,12)13)16-6(8-4)7(9)10/h2,6H,3H2,1H3,(H,9,10)(H2,11,12,13)/b5-2-/t6-/m1/s1 PQMCQNOVNFNPFJ-HYIMLASBSA-N logp -0.55 ALOGPS logs -1.47 ALOGPS solubility 9.10e+00 g/l ALOGPS logp -0.31 ChemAxon pka_strongest_acidic 1.67 ChemAxon pka_strongest_basic 0.31 ChemAxon iupac (2R,5Z)-4-methyl-5-[2-(phosphonooxy)ethylidene]-2,5-dihydro-1,3-thiazole-2-carboxylic acid ChemAxon average_mass 267.19 ChemAxon mono_mass 266.996645218 ChemAxon smiles CC1=N[C@H](S\C1=C/COP(O)(O)=O)C(O)=O ChemAxon formula C7H10NO6PS ChemAxon inchi InChI=1S/C7H10NO6PS/c1-4-5(2-3-14-15(11,12)13)16-6(8-4)7(9)10/h2,6H,3H2,1H3,(H,9,10)(H2,11,12,13)/b5-2-/t6-/m1/s1 ChemAxon inchikey PQMCQNOVNFNPFJ-HYIMLASBSA-N ChemAxon polar_surface_area 116.42 ChemAxon refractivity 58.03 ChemAxon polarizability 22.5 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Thiamine metabolism ec00730 Metabolic pathways eco01100 Specdb::CMs 1087572 Specdb::NmrOneD 320511 Specdb::NmrOneD 320512 Specdb::NmrOneD 320513 Specdb::NmrOneD 320514 Specdb::NmrOneD 320515 Specdb::NmrOneD 320516 Specdb::NmrOneD 320517 Specdb::NmrOneD 320518 Specdb::NmrOneD 320519 Specdb::NmrOneD 320520 Specdb::NmrOneD 320521 Specdb::NmrOneD 320522 Specdb::NmrOneD 320523 Specdb::NmrOneD 320524 Specdb::NmrOneD 320525 Specdb::NmrOneD 320526 Specdb::NmrOneD 320527 Specdb::NmrOneD 320528 Specdb::NmrOneD 320529 Specdb::NmrOneD 320530 Specdb::MsMs 23297 Specdb::MsMs 23298 Specdb::MsMs 23299 Specdb::MsMs 30095 Specdb::MsMs 30096 Specdb::MsMs 30097 C20246 Thiazole synthase P30139 THIG_ECOLI thiG http://ecmdb.ca/proteins/P30139.xml 1-Deoxy-D-xylulose 5-phosphate + 2-iminoacetate <> 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate +2 Water R10247 1-Deoxy-D-xylulose 5-phosphate + 2 2-iminoacetate <>2 2-[(2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate +2 Water