1.0 2011-09-21 00:24:13 UTC 2015-10-09 22:32:35 UTC FDB023069 Methylimidazoleacetic acid Methylimidazoleacetic acid is the main metabolite of histamine. This end product of histamine catabolism is formed by N-methylation in the imidazole ring to methylhistamine by histamine methyltransferase (EC 2.1.1.8) and a subsequent oxidative deamination in the side chain by type B monoamine oxidase (EC 1.4.3.4). From studies is known that as much as 70 to 80 percent of the histamine metabolized in the body is excreted in the urine as Methylimidazoleacetic acid. Thus, urinary Methylimidazoleacetic acid being the major and specific histamine metabolite is a clear marker of any changes in histamine metabolism in the body. The urinary excretion of methylimidazoleacetic acid is considered a reliable indicator of histamine turnover rate in the body. The excretion of Methylimidazoleacetic acid is higher in men than women however; this gender difference is abolished when corrected for creatinine excretion. A possible explanation is that basal histamine turnover is related to body size. There is no significant difference in Methylimidazoleacetic acid excretion between smokers and non-smokers when analysing absolute values (mg/24 h). When using Methylimidazoleacetic acid values corrected for creatinine excretion female smokers have significantly higher Methylimidazoleacetic acid excretion compared to nonsmokers. (PMID: 11411609, 7130180, 10350179, 10202992) [HMDB] 1-methyl-1H-Imidazole-4-acetate 1-methyl-1H-Imidazole-4-acetic acid 1-Methyl-4-imidazoleacetate 1-Methyl-4-imidazoleacetic acid 1-Methylimidazole-4-acetate 1-Methylimidazole-4-acetic acid 1,4-Methyl-imidazoleacetate 1,4-methyl-imidazoleacetic acid 1,4-Methylimidazoleacetate Methylimidazole acetate Methylimidazoleacetate Methylimidazoleacetic acid MIAA N tau-methylimidazoleacetic acid Tele-methylimidazoleacetate Tele-methylimidazoleacetic acid C6H8N2O2 140.1399 140.05857751 2-(1-methyl-1H-imidazol-4-yl)acetic acid methylimidazoleacetic acid 2625-49-2 CN1C=NC(CC(O)=O)=C1 InChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10) ZHCKPJGJQOPTLB-UHFFFAOYSA-N belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Imidazolyl carboxylic acids and derivatives Organic compounds Organoheterocyclic compounds Azoles Imidazoles Aromatic heteromonocyclic compounds Azacyclic compounds Carbonyl compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives N-substituted imidazoles Organic oxides Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Carbonyl group Carboxylic acid Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Imidazolyl carboxylic acid derivative Monocarboxylic acid or derivatives N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound imidazolyl carboxylic acid Solid logp -0.22 ALOGPS logs -1.38 ALOGPS solubility 5.88e+00 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 3.68 ChemAxon pka_strongest_basic 6.45 ChemAxon iupac 2-(1-methyl-1H-imidazol-4-yl)acetic acid ChemAxon average_mass 140.1399 ChemAxon mono_mass 140.05857751 ChemAxon smiles CN1C=NC(CC(O)=O)=C1 ChemAxon formula C6H8N2O2 ChemAxon inchi InChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10) ChemAxon inchikey ZHCKPJGJQOPTLB-UHFFFAOYSA-N ChemAxon polar_surface_area 55.12 ChemAxon refractivity 34.85 ChemAxon polarizability 13.69 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Histidine Metabolism SMP00044 map00340 Specdb::NmrTwoD 1841 Specdb::MsIr 1835 Specdb::MsIr 1836 Specdb::MsIr 1837 Specdb::CMs 1223 Specdb::CMs 9982 Specdb::CMs 31426 Specdb::CMs 38481 Specdb::CMs 145952 Specdb::NmrOneD 1906 Specdb::NmrOneD 149360 Specdb::NmrOneD 149361 Specdb::NmrOneD 149362 Specdb::NmrOneD 149363 Specdb::NmrOneD 149364 Specdb::NmrOneD 149365 Specdb::NmrOneD 149366 Specdb::NmrOneD 149367 Specdb::NmrOneD 149368 Specdb::NmrOneD 149369 Specdb::NmrOneD 149370 Specdb::NmrOneD 149371 Specdb::NmrOneD 149372 Specdb::NmrOneD 149373 Specdb::NmrOneD 149374 Specdb::NmrOneD 149375 Specdb::NmrOneD 149376 Specdb::NmrOneD 149377 Specdb::NmrOneD 149378 Specdb::NmrOneD 149379 Specdb::MsMs 2140 Specdb::MsMs 2141 Specdb::MsMs 2142 Specdb::MsMs 288073 Specdb::MsMs 288074 Specdb::MsMs 288075 Specdb::MsMs 327070 Specdb::MsMs 327071 Specdb::MsMs 327072 Specdb::MsMs 1448478 Specdb::MsMs 2237962 Specdb::MsMs 2239626 Specdb::MsMs 2244150 Specdb::MsMs 2245961 Specdb::MsMs 2246296 Specdb::MsMs 2247968 Specdb::MsMs 2248421 Specdb::MsMs 2249967 Specdb::MsMs 2250385 Specdb::MsMs 2251988 Specdb::MsMs 2456046 Specdb::MsMs 2456047 Specdb::MsMs 2456048 Specdb::MsMs 2478787 Specdb::MsMs 2478788 HMDB02820 #<Reference:0x000055ce31c49118> #<Reference:0x000055ce31c48f60> #<Reference:0x000055ce31c48da8> #<Reference:0x000055ce31c48bf0> #<Reference:0x000055ce31c48a38> #<Reference:0x000055ce31c48880> #<Reference:0x000055ce31c486a0> #<Reference:0x000055ce31c484e8> #<Reference:0x000055ce31c48308> #<Reference:0x000055ce31c48150> #<Reference:0x000055ce317bbfb0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823