2.0 2012-05-31 14:24:37 -0600 2015-09-18 09:17:42 -0600 ECMDB20046 M2MDB000895 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate is a member of the chemical class known as Organic Pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. HMP-PP is involved in thiamin biosynthesis. Two redundant genes, THI20 and THI21, of Saccharomyces cerevisiae encode a 2-methyl-4-amino-5-hydroxymethylpyrimidine monophosphate (HMP-P) kinase required for thiamin biosynthesis. Although each isoform independently can synthesize HMP pyrophosphate (HMP-PP) from HMP, there is a marked difference in efficiency between the two proteins. (PMID 15614489) (4-amino-2-methylpyrimidin-5-yl)methyl diphosphate (4-amino-2-Methylpyrimidin-5-yl)methyl diphosphoric acid 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphoric acid 4-Amino-2-methyl-5-diphosphomethylpyrimidine 4-Amino-5-hydroxymethyl-2-methylpyrimidine-PP 4A5HMe2MePyrPP HMP-PP C6H8N3O7P2 296.093 295.985394345 {[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl phosphonato]oxy}phosphonate [(4-imino-2-methyl-3H-pyrimidin-5-yl)methyl phosphonato]oxyphosphonate CC1=NC=C(COP([O-])(=O)OP([O-])([O-])=O)C(=N)N1 InChI=1S/C6H11N3O7P2/c1-4-8-2-5(6(7)9-4)3-15-18(13,14)16-17(10,11)12/h2H,3H2,1H3,(H,13,14)(H2,7,8,9)(H2,10,11,12)/p-3 AGQJQCFEPUVXNK-UHFFFAOYSA-K Cytosol logp -0.34 ALOGPS logs -1.46 ALOGPS solubility 1.22e+01 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic 12.19 ChemAxon iupac {[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl phosphonato]oxy}phosphonate ChemAxon average_mass 296.093 ChemAxon mono_mass 295.985394345 ChemAxon smiles CC1=NC=C(COP([O-])(=O)OP([O-])([O-])=O)C(=N)N1 ChemAxon formula C6H8N3O7P2 ChemAxon inchi InChI=1S/C6H11N3O7P2/c1-4-8-2-5(6(7)9-4)3-15-18(13,14)16-17(10,11)12/h2H,3H2,1H3,(H,13,14)(H2,7,8,9)(H2,10,11,12)/p-3 ChemAxon inchikey AGQJQCFEPUVXNK-UHFFFAOYSA-K ChemAxon polar_surface_area 170.02 ChemAxon refractivity 66.33 ChemAxon polarizability 22.61 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 8 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge -3 ChemAxon Thiamine metabolism ec00730 Metabolic pathways eco01100 Vitamin B1/Thiamine PW000892 Metabolic Thiamin diphosphate biosynthesis PW002028 Metabolic 4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis PWY-6890 thiamin diphosphate biosynthesis I (E. coli) PWY-6894 Specdb::NmrOneD 283909 Specdb::NmrOneD 283910 Specdb::NmrOneD 283911 Specdb::NmrOneD 283912 Specdb::NmrOneD 283913 Specdb::NmrOneD 283914 Specdb::NmrOneD 283915 Specdb::NmrOneD 283916 Specdb::NmrOneD 283917 Specdb::NmrOneD 283918 Specdb::NmrOneD 283919 Specdb::NmrOneD 283920 Specdb::NmrOneD 283921 Specdb::NmrOneD 283922 Specdb::NmrOneD 283923 Specdb::NmrOneD 283924 Specdb::NmrOneD 283925 Specdb::NmrOneD 283926 Specdb::NmrOneD 283927 Specdb::NmrOneD 283928 217 212 C04752 16629 AMINO-HYDROXYMETHYL-METHYLPYRIMIDINE-PP Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Kawasaki, Y., Onozuka, M., Mizote, T., Nosaka, K. (2005). "Biosynthesis of hydroxymethylpyrimidine pyrophosphate in Saccharomyces cerevisiae." Curr Genet 47:156-162. 15614489 Phosphatase nudJ P0AEI6 NUDJ_ECOLI nudJ http://ecmdb.ca/proteins/P0AEI6.xml Thiamine-phosphate pyrophosphorylase P30137 THIE_ECOLI thiE http://ecmdb.ca/proteins/P30137.xml HMP-PP phosphatase P46891 COF_ECOLI cof http://ecmdb.ca/proteins/P46891.xml Hydroxymethylpyrimidine/phosphomethylpyrimidine kinase P76422 THID_ECOLI thiD http://ecmdb.ca/proteins/P76422.xml 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Water > 4-Amino-2-methyl-5-phosphomethylpyrimidine + Hydrogen ion + Phosphate RXN0-3543 4-Amino-2-methyl-5-phosphomethylpyrimidine + Adenosine triphosphate > 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + ADP R04509 PYRIMSYN3-RXN 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate R03223 THI-P-SYN-RXN 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole <> Pyrophosphate + Thiamine monophosphate R03223 Adenosine triphosphate + 4-Amino-2-methyl-5-phosphomethylpyrimidine <> ADP + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate R04509 2-[(2R,5Z)-(2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Hydrogen ion > Thiamine monophosphate + Carbon dioxide + Pyrophosphate RXN-12611 Hydrogen ion + 4-Methyl-5-(2-phosphoethyl)-thiazole + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Pyrophosphate THI-P-SYN-RXN 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole > Pyrophosphate + Thiamine monophosphate 4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + 2 Hydrogen ion + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Carbon dioxide + diphosphate + Thiamine monophosphate + Pyrophosphate PW_R003336 Pyridoxal 5'-phosphate > 4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate PW_R003338 4-amino-2-methyl-5-phosphomethylpyrimidine + Adenosine triphosphate > ADP + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate PW_R005932 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + Hydrogen ion > Carbon dioxide + Pyrophosphate + Thiamine monophosphate PW_R005933 2 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate