2.02012-05-31 14:24:37 -06002015-09-18 09:17:42 -0600ECMDB20046M2MDB0008952-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate2-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 acid2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphoric acid4-Amino-2-methyl-5-diphosphomethylpyrimidine4-Amino-5-hydroxymethyl-2-methylpyrimidine-PP4A5HMe2MePyrPPHMP-PPC6H8N3O7P2296.093295.985394345{[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl phosphonato]oxy}phosphonate[(4-imino-2-methyl-3H-pyrimidin-5-yl)methyl phosphonato]oxyphosphonateCC1=NC=C(COP([O-])(=O)OP([O-])([O-])=O)C(=N)N1InChI=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-3AGQJQCFEPUVXNK-UHFFFAOYSA-KCytosollogp-0.34logs-1.46solubility1.22e+01 g/llogp-2.8pka_strongest_acidic1.74pka_strongest_basic12.19iupac{[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl phosphonato]oxy}phosphonateaverage_mass296.093mono_mass295.985394345smilesCC1=NC=C(COP([O-])(=O)OP([O-])([O-])=O)C(=N)N1formulaC6H8N3O7P2inchiInChI=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-3inchikeyAGQJQCFEPUVXNK-UHFFFAOYSA-Kpolar_surface_area170.02refractivity66.33polarizability22.61rotatable_bond_count5acceptor_count8donor_count2physiological_charge-1formal_charge-3Thiamine metabolismec00730Metabolic pathwayseco01100Vitamin B1/ThiaminePW000892MetabolicThiamin diphosphate biosynthesisPW002028Metabolic4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesisPWY-6890thiamin diphosphate biosynthesis I (E. coli)PWY-6894Specdb::NmrOneD283909Specdb::NmrOneD283910Specdb::NmrOneD283911Specdb::NmrOneD283912Specdb::NmrOneD283913Specdb::NmrOneD283914Specdb::NmrOneD283915Specdb::NmrOneD283916Specdb::NmrOneD283917Specdb::NmrOneD283918Specdb::NmrOneD283919Specdb::NmrOneD283920Specdb::NmrOneD283921Specdb::NmrOneD283922Specdb::NmrOneD283923Specdb::NmrOneD283924Specdb::NmrOneD283925Specdb::NmrOneD283926Specdb::NmrOneD283927Specdb::NmrOneD283928217212C0475216629AMINO-HYDROXYMETHYL-METHYLPYRIMIDINE-PPKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Kawasaki, Y., Onozuka, M., Mizote, T., Nosaka, K. (2005). "Biosynthesis of hydroxymethylpyrimidine pyrophosphate in Saccharomyces cerevisiae." Curr Genet 47:156-162.15614489Phosphatase nudJP0AEI6NUDJ_ECOLInudJhttp://ecmdb.ca/proteins/P0AEI6.xmlThiamine-phosphate pyrophosphorylaseP30137THIE_ECOLIthiEhttp://ecmdb.ca/proteins/P30137.xmlHMP-PP phosphataseP46891COF_ECOLIcofhttp://ecmdb.ca/proteins/P46891.xmlHydroxymethylpyrimidine/phosphomethylpyrimidine kinaseP76422THID_ECOLIthiDhttp://ecmdb.ca/proteins/P76422.xml2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Water > 4-Amino-2-methyl-5-phosphomethylpyrimidine + Hydrogen ion + PhosphateRXN0-35434-Amino-2-methyl-5-phosphomethylpyrimidine + Adenosine triphosphate > 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + ADPR04509PYRIMSYN3-RXN2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphateR03223THI-P-SYN-RXN2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole <> Pyrophosphate + Thiamine monophosphateR03223Adenosine triphosphate + 4-Amino-2-methyl-5-phosphomethylpyrimidine <> ADP + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphateR045092-[(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 + PyrophosphateRXN-12611Hydrogen ion + 4-Methyl-5-(2-phosphoethyl)-thiazole + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + PyrophosphateTHI-P-SYN-RXN2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole > Pyrophosphate + Thiamine monophosphate4-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 + PyrophosphatePW_R003336Pyridoxal 5'-phosphate > 4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphatePW_R0033384-amino-2-methyl-5-phosphomethylpyrimidine + Adenosine triphosphate > ADP + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphatePW_R0059322-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + Hydrogen ion > Carbon dioxide + Pyrophosphate + Thiamine monophosphatePW_R0059332 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate