2.0 2012-05-31 14:26:35 -0600 2015-10-15 16:14:23 -0600 ECMDB20084 M2MDB000932 4-Amino-2-methyl-5-phosphomethylpyrimidine 4-amino-2-methyl-5-phosphomethylpyrimidine is a member of the chemical class known as Pyrimidines and Pyrimidine Derivatives. These are compounds containing a pyrimidne ring, which is a six-member aromatic heterocycle which consists of two nitrogen atoms (at positions 1 and 3) and four carbon atoms. Tomato LeTHIC is an Fe-requiring HMP-P synthase involved in thiamine synthesis and regulated by multiple factors. (PMID 21511719) 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 dihydrogen phosphate (4-amino-2-Methylpyrimidin-5-yl)methyl dihydrogen phosphoric acid 4-Amino-5-hydroxymethyl-2-methylpyrimidine-P 4-Amino-5-hydroxymethyl-2-methylpyrimidine-phosphate 4-amino-5-Hydroxymethyl-2-methylpyrimidine-phosphoric acid 4-Amino-5-phosphomethyl-2-methylpyrimidine HMePyrP HMP-P C6H8N3O4P 217.122 217.026339907 [(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methoxy]phosphonic acid (4-imino-2-methyl-3H-pyrimidin-5-yl)methoxyphosphonic acid CC1=NC=C(COP([O-])([O-])=O)C(=N)N1 InChI=1S/C6H10N3O4P/c1-4-8-2-5(6(7)9-4)3-13-14(10,11)12/h2H,3H2,1H3,(H2,7,8,9)(H2,10,11,12)/p-2 PKYFHKIYHBRTPI-UHFFFAOYSA-L Cytosol logp -1.06 ALOGPS logs -2.46 ALOGPS solubility 7.57e-01 g/l ALOGPS logp -1.8 ChemAxon pka_strongest_acidic 1.62 ChemAxon pka_strongest_basic 7.59 ChemAxon iupac [(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methoxy]phosphonic acid ChemAxon average_mass 217.122 ChemAxon mono_mass 217.026339907 ChemAxon smiles CC1=NC=C(COP([O-])([O-])=O)C(=N)N1 ChemAxon formula C6H8N3O4P ChemAxon inchi InChI=1S/C6H10N3O4P/c1-4-8-2-5(6(7)9-4)3-13-14(10,11)12/h2H,3H2,1H3,(H2,7,8,9)(H2,10,11,12)/p-2 ChemAxon inchikey PKYFHKIYHBRTPI-UHFFFAOYSA-L ChemAxon polar_surface_area 115 ChemAxon refractivity 58.83 ChemAxon polarizability 18.83 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Thiamine metabolism ec00730 Metabolic pathways eco01100 4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis PWY-6890 Specdb::CMs 3425 Specdb::CMs 126720 Specdb::NmrOneD 182141 Specdb::NmrOneD 182142 Specdb::NmrOneD 182143 Specdb::NmrOneD 182144 Specdb::NmrOneD 182145 Specdb::NmrOneD 182146 Specdb::NmrOneD 182147 Specdb::NmrOneD 182148 Specdb::NmrOneD 182149 Specdb::NmrOneD 182150 Specdb::NmrOneD 182151 Specdb::NmrOneD 182152 Specdb::NmrOneD 182153 Specdb::NmrOneD 182154 Specdb::NmrOneD 182155 Specdb::NmrOneD 182156 Specdb::NmrOneD 182157 Specdb::NmrOneD 182158 Specdb::NmrOneD 182159 Specdb::NmrOneD 182160 Specdb::MsMs 24902 Specdb::MsMs 24903 Specdb::MsMs 24904 Specdb::MsMs 31460 Specdb::MsMs 31461 Specdb::MsMs 31462 Specdb::MsMs 3391456 Specdb::MsMs 3391457 Specdb::MsMs 3391458 Specdb::MsMs 3391459 Specdb::MsMs 3391460 Specdb::MsMs 3391461 216 211 C04556 18032 AMINO-HYDROXYMETHYL-METHYL-PYR-P MP5 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 Zhao, W., Cheng, X., Huang, Z., Fan, H., Wu, H., Ling, H. Q. (2011). "Tomato LeTHIC is an Fe-requiring HMP-P synthase involved in thiamine synthesis and regulated by multiple factors." Plant Cell Physiol 52:967-982. 21511719 Phosphatase nudJ P0AEI6 NUDJ_ECOLI nudJ http://ecmdb.ca/proteins/P0AEI6.xml Pyridoxine kinase P40191 PDXK_ECOLI pdxK http://ecmdb.ca/proteins/P40191.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 Phosphomethylpyrimidine synthase P30136 THIC_ECOLI thiC http://ecmdb.ca/proteins/P30136.xml 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Water > 4-Amino-2-methyl-5-phosphomethylpyrimidine + Hydrogen ion + Phosphate RXN0-3543 4-Amino-5-hydroxymethyl-2-methylpyrimidine + Adenosine triphosphate <> 4-Amino-2-methyl-5-phosphomethylpyrimidine + ADP + Hydrogen ion + 4-amino-5-phosphonooxymethyl-2-methylpyrimidine R03471 OHMETPYRKIN-RXN 4-Amino-2-methyl-5-phosphomethylpyrimidine + Adenosine triphosphate > 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + ADP R04509 PYRIMSYN3-RXN 5-Aminoimidazole ribonucleotide + Water + NAD > 4-Amino-2-methyl-5-phosphomethylpyrimidine +2 Formic acid +3 Hydrogen ion + NADH Adenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine <> ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine R03471 Adenosine triphosphate + 4-Amino-2-methyl-5-phosphomethylpyrimidine <> ADP + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate R04509 Adenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine <> Hydrogen ion + ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine OHMETPYRKIN-RXN 5-Aminoimidazole ribonucleotide + S-Adenosylmethionine 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + carbon monoxide + Hydrogen ion PYRIMSYN1-RXN 5-Aminoimidazole ribonucleotide + S-adenosyl-L-methionine > 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO Adenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine > ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <> 5-Aminoimidazole ribonucleotide + 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO R03472 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + Adenosine triphosphate <>4 4-Amino-2-methyl-5-phosphomethylpyrimidine + ADP + Hydrogen ion +4 4-amino-5-phosphonooxymethyl-2-methylpyrimidine 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + Adenosine triphosphate <>4 4-Amino-2-methyl-5-phosphomethylpyrimidine + ADP + Hydrogen ion +4 4-amino-5-phosphonooxymethyl-2-methylpyrimidine 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO