2.02012-05-31 14:26:41 -06002015-06-03 17:19:17 -0600ECMDB20086M2MDB0009344-Amino-5-hydroxymethyl-2-methylpyrimidine4-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)methanol2-M-4-A-5-Hmp2-Methyl-4-amino-5-hydroxymethylpyrimidine4-Amino-2-methyl-5-hydroxymethylpyrimidine4-Amino-2-methyl-5-pyrimidinemethanol4-amino-5-hydroxymethyl-2-methylpyrimidine5-Pyrimidinemethanol, 4-amino-2-methyl- (8CI)(9CI)6-Amino-5-hydroxymethyl-2-methylpyrimidineAtoxopyrimidineHMePyrHMHHMPHydroxymethylpyrimidineNchembio.121-comp11NChemBio.2007.13-comp6OMPMOxymethylpyrimidinePyraminPyramin (van)PyraminePyramine (thiamine metabolite)Pyramine (van)PyrazanToxopyrimidineTXPC6H9N3O139.1552139.074561925(4-amino-2-methylpyrimidin-5-yl)methanoltoxopyrimidine73-67-6CC1=NC=C(CO)C(N)=N1InChI=1S/C6H9N3O/c1-4-8-2-5(3-10)6(7)9-4/h2,10H,3H2,1H3,(H2,7,8,9)VUTBELPREDJDDH-UHFFFAOYSA-NSolidCytosollogp-0.26logs-1.06solubility1.20e+01 g/lmelting_point198 oClogp-0.36pka_strongest_acidic14.41pka_strongest_basic6.17iupac(4-amino-2-methylpyrimidin-5-yl)methanolaverage_mass139.1552mono_mass139.074561925smilesCC1=NC=C(CO)C(N)=N1formulaC6H9N3OinchiInChI=1S/C6H9N3O/c1-4-8-2-5(3-10)6(7)9-4/h2,10H,3H2,1H3,(H2,7,8,9)inchikeyVUTBELPREDJDDH-UHFFFAOYSA-Npolar_surface_area72.03refractivity39.18polarizability14.2rotatable_bond_count1acceptor_count4donor_count2physiological_charge0formal_charge0Thiamine metabolismec00730ABC transportersec02010Metabolic pathwayseco01100Specdb::CMs2384Specdb::CMs129580Specdb::CMs831019Specdb::CMs831020Specdb::CMs831021Specdb::CMs831022Specdb::NmrOneD202187Specdb::NmrOneD202188Specdb::NmrOneD202189Specdb::NmrOneD202190Specdb::NmrOneD202191Specdb::NmrOneD202192Specdb::NmrOneD202193Specdb::NmrOneD202194Specdb::NmrOneD202195Specdb::NmrOneD202196Specdb::NmrOneD202197Specdb::NmrOneD202198Specdb::NmrOneD202199Specdb::NmrOneD202200Specdb::NmrOneD202201Specdb::NmrOneD202202Specdb::NmrOneD202203Specdb::NmrOneD202204Specdb::NmrOneD202205Specdb::NmrOneD202206Specdb::MsMs20747Specdb::MsMs20748Specdb::MsMs20749Specdb::MsMs22298Specdb::MsMs22299Specdb::MsMs22300Specdb::MsMs3410297Specdb::MsMs3410298Specdb::MsMs3410299Specdb::MsMs3410300Specdb::MsMs3410301Specdb::MsMs3410302777756C0127916892HMPHMHKeseler, I. 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Org Biomol Chem 2:2538-2546.15326535Pyridoxine kinaseP40191PDXK_ECOLIpdxKhttp://ecmdb.ca/proteins/P40191.xmlHydroxymethylpyrimidine/phosphomethylpyrimidine kinaseP76422THID_ECOLIthiDhttp://ecmdb.ca/proteins/P76422.xmlPhosphomethylpyrimidine synthaseP30136THIC_ECOLIthiChttp://ecmdb.ca/proteins/P30136.xml4-Amino-5-hydroxymethyl-2-methylpyrimidine + Adenosine triphosphate <> 4-Amino-2-methyl-5-phosphomethylpyrimidine + ADP + Hydrogen ion + 4-amino-5-phosphonooxymethyl-2-methylpyrimidineR03471OHMETPYRKIN-RXNAdenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine <> ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidineR034714-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <> 5-Aminoimidazole ribonucleotide + 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + COR03472Adenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine <> Hydrogen ion + ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidineOHMETPYRKIN-RXNAdenosine triphosphate + 4-Amino-5-hydroxymethyl-2-methylpyrimidine > ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + Adenosine triphosphate <>4 4-Amino-2-methyl-5-phosphomethylpyrimidine + ADP + Hydrogen ion +4 4-amino-5-phosphonooxymethyl-2-methylpyrimidine4 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 + CO4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + Adenosine triphosphate <>4 4-Amino-2-methyl-5-phosphomethylpyrimidine + ADP + Hydrogen ion +4 4-amino-5-phosphonooxymethyl-2-methylpyrimidine4 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