2.0 2012-05-31 13:56:55 -0600 2015-09-17 15:41:16 -0600 ECMDB02666 M2MDB000462 Thiamine monophosphate Thiamine dihydrogen phosphate ester. The monophosphate ester of thiamine. Synonyms: monophosphothiamine; vitamin B1 monophosphate. -- Pubchem Aneurin-monophosphorsaeureester Aneurine monophosphate Aneurine monophosphoric acid Monofosfotiamina Monophosphoric ester of thiamine Monophosphothiamine Monophosphothiaminum Phosphothiaminum Thiamin dihydrogenphosphate Thiamin dihydrogenphosphoric acid Thiamin monophosphate Thiamin monophosphoric acid Thiamin phosphate Thiamin phosphoric acid Thiamin-P Thiamine monophosphate Thiamine monophosphate dihydrate Thiamine monophosphoric acid Thiamine monophosphoric acid dihydric acid Thiamine phosphate Thiamine phosphoric acid Thiamine-phosphate Thiamine-phosphoric acid Thiamine-Pi ThiamineP ThP Tiamina monofosfato TMP C12H17N4O4PS 344.327 344.070812254 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium thiamin monophosphate 495-23-8 CC1=C(CCO[P@](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19) HZSAJDVWZRBGIF-UHFFFAOYSA-N Solid Cytosol logp -1.63 ALOGPS logs -3.92 ALOGPS solubility 4.56e-02 g/l ALOGPS logp -5.7 ChemAxon pka_strongest_acidic 1.66 ChemAxon pka_strongest_basic 5.51 ChemAxon iupac 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium ChemAxon average_mass 344.327 ChemAxon mono_mass 344.070812254 ChemAxon smiles CC1=C(CCO[P@](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N ChemAxon formula C12H17N4O4PS ChemAxon inchi InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19) ChemAxon inchikey HZSAJDVWZRBGIF-UHFFFAOYSA-N ChemAxon polar_surface_area 122.44 ChemAxon refractivity 84.27 ChemAxon polarizability 32.59 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 1 ChemAxon Thiamine metabolism ec00730 Metabolic pathways eco01100 Vitamin B1/Thiamine PW000892 Metabolic Thiamin diphosphate biosynthesis PW002028 Metabolic thiamin diphosphate biosynthesis I (E. coli) PWY-6894 Specdb::CMs 149535 Specdb::NmrOneD 4965 Specdb::NmrOneD 4966 Specdb::NmrOneD 122798 Specdb::NmrOneD 122799 Specdb::NmrOneD 122800 Specdb::NmrOneD 122801 Specdb::NmrOneD 122802 Specdb::NmrOneD 122803 Specdb::NmrOneD 122804 Specdb::NmrOneD 122805 Specdb::NmrOneD 122806 Specdb::NmrOneD 122807 Specdb::NmrOneD 122808 Specdb::NmrOneD 122809 Specdb::NmrOneD 122810 Specdb::NmrOneD 122811 Specdb::NmrOneD 122812 Specdb::NmrOneD 122813 Specdb::NmrOneD 122814 Specdb::NmrOneD 122815 Specdb::NmrOneD 122816 Specdb::NmrOneD 122817 Specdb::MsMs 24620 Specdb::MsMs 24621 Specdb::MsMs 24622 Specdb::MsMs 31178 Specdb::MsMs 31179 Specdb::MsMs 31180 Specdb::MsMs 2235962 Specdb::MsMs 2237444 Specdb::MsMs 2238023 Specdb::MsMs 2239530 Specdb::MsMs 2934333 Specdb::MsMs 2934334 Specdb::MsMs 2934335 HMDB02666 1131 2627905 C01081 9533 THIAMINE-P TPS Thiamine monophosphate 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 Leder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71. http://hmdb.ca/system/metabolites/msds/000/002/249/original/HMDB02666.pdf?1358462099 Phosphatase nudJ P0AEI6 NUDJ_ECOLI nudJ http://ecmdb.ca/proteins/P0AEI6.xml Thiamine-monophosphate kinase P0AGG0 THIL_ECOLI thiL http://ecmdb.ca/proteins/P0AGG0.xml Thiamine-phosphate pyrophosphorylase P30137 THIE_ECOLI thiE http://ecmdb.ca/proteins/P30137.xml Thiamine kinase P75948 THIK_ECOLI thiK http://ecmdb.ca/proteins/P75948.xml Adenosine triphosphate + Thiamine monophosphate <> ADP + Thiamine pyrophosphate R00617 THI-P-KIN-RXN Adenosine triphosphate + Thiamine <> ADP + Hydrogen ion + Thiamine monophosphate R02134 THIKIN-RXN Water + Thiamine pyrophosphate > Hydrogen ion + Phosphate + Thiamine monophosphate RXN0-3542 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate R03223 THI-P-SYN-RXN Adenosine triphosphate + Thiamine <> ADP + Thiamine monophosphate R02134 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole <> Pyrophosphate + Thiamine monophosphate R03223 2-[(2<i>R</i>,5<i>Z</i>)-(2-carboxy-4-methylthiazol-5(2<i>H</i>)-ylidene]ethyl phosphate + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Hydrogen ion > Thiamine monophosphate + Carbon dioxide + Pyrophosphate RXN-12611 Thiamine monophosphate + Adenosine triphosphate > Thiamine pyrophosphate + ADP THI-P-KIN-RXN Hydrogen ion + 4-Methyl-5-(2-phosphoethyl)-thiazole + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Pyrophosphate THI-P-SYN-RXN Thiamine + Adenosine triphosphate > Hydrogen ion + Thiamine monophosphate + ADP THIKIN-RXN 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole > Pyrophosphate + Thiamine monophosphate Adenosine triphosphate + Thiamine > ADP + 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 Thiamine monophosphate + Adenosine triphosphate + Thiamine monophosphate > Thiamine pyrophosphate + Adenosine diphosphate + ADP PW_R003337 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 Adenosine triphosphate + Thiamine monophosphate <> ADP + Thiamine pyrophosphate