2.0 2012-05-31 14:26:41 -0600 2015-06-03 17:19:17 -0600 ECMDB20086 M2MDB000934 4-Amino-5-hydroxymethyl-2-methylpyrimidine 4-amino-5-hydroxymethyl-2-methylpyrimidine 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. The conversion of 5-aminoimidazole ribonucleotide (AIR) into 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP) is a fascinating reaction on the thiamin biosynthetic pathway in bacteria and is probably the most complex unresolved rearrangement in primary metabolism. (PMID 15326535) (4-Amino-2-methyl-5-pyrimidinyl)methanol (4-amino-2-methylpyrimidin-5-yl)methanol 2-M-4-A-5-Hmp 2-Methyl-4-amino-5-hydroxymethylpyrimidine 4-Amino-2-methyl-5-hydroxymethylpyrimidine 4-Amino-2-methyl-5-pyrimidinemethanol 4-amino-5-hydroxymethyl-2-methylpyrimidine 5-Pyrimidinemethanol, 4-amino-2-methyl- (8CI)(9CI) 6-Amino-5-hydroxymethyl-2-methylpyrimidine Atoxopyrimidine HMePyr HMH HMP Hydroxymethylpyrimidine Nchembio.121-comp11 NChemBio.2007.13-comp6 OMPM Oxymethylpyrimidine Pyramin Pyramin (van) Pyramine Pyramine (thiamine metabolite) Pyramine (van) Pyrazan Toxopyrimidine TXP C6H9N3O 139.1552 139.074561925 (4-amino-2-methylpyrimidin-5-yl)methanol toxopyrimidine 73-67-6 CC1=NC=C(CO)C(N)=N1 InChI=1S/C6H9N3O/c1-4-8-2-5(3-10)6(7)9-4/h2,10H,3H2,1H3,(H2,7,8,9) VUTBELPREDJDDH-UHFFFAOYSA-N Solid Cytosol logp -0.26 ALOGPS logs -1.06 ALOGPS solubility 1.20e+01 g/l ALOGPS melting_point 198 oC logp -0.36 ChemAxon pka_strongest_acidic 14.41 ChemAxon pka_strongest_basic 6.17 ChemAxon iupac (4-amino-2-methylpyrimidin-5-yl)methanol ChemAxon average_mass 139.1552 ChemAxon mono_mass 139.074561925 ChemAxon smiles CC1=NC=C(CO)C(N)=N1 ChemAxon formula C6H9N3O ChemAxon inchi InChI=1S/C6H9N3O/c1-4-8-2-5(3-10)6(7)9-4/h2,10H,3H2,1H3,(H2,7,8,9) ChemAxon inchikey VUTBELPREDJDDH-UHFFFAOYSA-N ChemAxon polar_surface_area 72.03 ChemAxon refractivity 39.18 ChemAxon polarizability 14.2 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Thiamine metabolism ec00730 ABC transporters ec02010 Metabolic pathways eco01100 Specdb::CMs 2384 Specdb::CMs 129580 Specdb::CMs 831019 Specdb::CMs 831020 Specdb::CMs 831021 Specdb::CMs 831022 Specdb::NmrOneD 202187 Specdb::NmrOneD 202188 Specdb::NmrOneD 202189 Specdb::NmrOneD 202190 Specdb::NmrOneD 202191 Specdb::NmrOneD 202192 Specdb::NmrOneD 202193 Specdb::NmrOneD 202194 Specdb::NmrOneD 202195 Specdb::NmrOneD 202196 Specdb::NmrOneD 202197 Specdb::NmrOneD 202198 Specdb::NmrOneD 202199 Specdb::NmrOneD 202200 Specdb::NmrOneD 202201 Specdb::NmrOneD 202202 Specdb::NmrOneD 202203 Specdb::NmrOneD 202204 Specdb::NmrOneD 202205 Specdb::NmrOneD 202206 Specdb::MsMs 20747 Specdb::MsMs 20748 Specdb::MsMs 20749 Specdb::MsMs 22298 Specdb::MsMs 22299 Specdb::MsMs 22300 Specdb::MsMs 3410297 Specdb::MsMs 3410298 Specdb::MsMs 3410299 Specdb::MsMs 3410300 Specdb::MsMs 3410301 Specdb::MsMs 3410302 777 756 C01279 16892 HMP HMH 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Lawhorn, B. G., Mehl, R. A., Begley, T. P. (2004). "Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction." Org Biomol Chem 2:2538-2546. 15326535 Pyridoxine kinase P40191 PDXK_ECOLI pdxK http://ecmdb.ca/proteins/P40191.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 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 Adenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine <> ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine R03471 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 Adenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine <> Hydrogen ion + ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine OHMETPYRKIN-RXN Adenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine > ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine 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