1.0 2016-09-30 22:07:14 UTC 2020-06-04 20:10:20 UTC BMDB0000001 BMDB00001 1-Methylhistidine 1-Methylhistidine, also known as 1-mhis, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 1-Methylhistidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 1-Methylhistidine exists in all living organisms, ranging from bacteria to humans. 1-Methylhistidine participates in a number of enzymatic reactions, within cattle. In particular, 1-Methylhistidine and beta-alanine can be converted into anserine through its interaction with the enzyme carnosine synthase 1. In addition, beta-Alanine and 1-methylhistidine can be biosynthesized from anserine; which is mediated by the enzyme cytosolic non-specific dipeptidase. In cattle, 1-methylhistidine is involved in the metabolic pathway called the histidine metabolism pathway. 1-Methylhistidine has been found to be associated with several diseases known as eosinophilic esophagitis, early preeclampsia, and obesity; also 1-methylhistidine has been linked to several inborn metabolic disorders including maple syrup urine disease and propionic acidemia. (2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid (2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoate 1 Methylhistidine 1-Methyl histidine 1-Methyl-histidine 1-Methyl-L-histidine 1-MHis 1-N-Methyl-L-histidine L-1-Methylhistidine N1-Methyl-L-histidine 1-Methylhistidine dihydrochloride 1-Methylhistidine Tau methylhistidine N(Tau)-methylhistidine Tau-methyl-L-histidine N Tau-methylhistidine C7H11N3O2 169.1811 169.085126611 2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid hydrate 4-methyl-histidine hydrate 332-80-9 CN1C=NC(C[C@H](N)C(O)=O)=C1 InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1 BRMWTNUJHUMWMS-LURJTMIESA-N belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Histidine and derivatives Amino acids Aralkylamines Azacyclic compounds Carbonyl compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Imidazolyl carboxylic acids and derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives N-substituted imidazoles Organic oxides Organopnictogen compounds Alpha-amino acid Amine Amino acid Aralkylamine Aromatic heteromonocyclic compound Azacycle Azole Carbonyl group Carboxylic acid Heteroaromatic compound Histidine or derivatives Hydrocarbon derivative Imidazole Imidazolyl carboxylic acid derivative L-alpha-amino acid Monocarboxylic acid or derivatives N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Aromatic heteromonocyclic compounds L-histidine derivative non-proteinogenic L-alpha-amino acid Solid melting_point 249 http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf logp -2.95 ALOGPS logs -1.39 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.96 ChemAxon pka_strongest_basic 9.25 ChemAxon iupac 2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid hydrate ChemAxon average_mass 169.1811 ChemAxon mono_mass 169.085126611 ChemAxon smiles CN1C=NC(C[C@H](N)C(O)=O)=C1 ChemAxon formula C7H11N3O2 ChemAxon inchi InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1 ChemAxon inchikey BRMWTNUJHUMWMS-LURJTMIESA-N ChemAxon polar_surface_area 81.14 ChemAxon refractivity 42.39 ChemAxon polarizability 17.1 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Histidine Metabolism SMP0087219 Specdb::NmrTwoD 915 Specdb::MsIr 79 Specdb::MsIr 80 Specdb::MsIr 81 Specdb::MsMs 1 Specdb::MsMs 2 Specdb::MsMs 3 Specdb::MsMs 255159 Specdb::MsMs 255160 Specdb::MsMs 255161 Specdb::MsMs 275100 Specdb::MsMs 275101 Specdb::MsMs 275102 Specdb::MsMs 2346413 Specdb::MsMs 2346414 Specdb::MsMs 2346415 Specdb::MsMs 2593057 Specdb::MsMs 2593058 Specdb::MsMs 2593059 Specdb::CMs 1469 Specdb::CMs 1755 Specdb::CMs 7663 Specdb::CMs 30940 Specdb::CMs 30941 Specdb::CMs 37237 Specdb::CMs 166679 Specdb::CMs 1032476 Specdb::CMs 1032478 Specdb::CMs 1032480 Specdb::NmrOneD 1022 Specdb::NmrOneD 5292 Specdb::NmrOneD 5293 Specdb::NmrOneD 5294 Specdb::NmrOneD 5295 Specdb::NmrOneD 5296 Specdb::NmrOneD 5297 Specdb::NmrOneD 5298 Specdb::NmrOneD 5299 Specdb::NmrOneD 5300 Specdb::NmrOneD 5301 Specdb::NmrOneD 5302 Specdb::NmrOneD 5303 Specdb::NmrOneD 5304 Specdb::NmrOneD 5305 Specdb::NmrOneD 5306 Specdb::NmrOneD 5307 Specdb::NmrOneD 5308 Specdb::NmrOneD 5309 Specdb::NmrOneD 5310 Specdb::NmrOneD 5311 Blood Detected by NMR in multiparous-early lactation Holstein cows. Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17. 24440255 Blood Jiyuan Li, Everestus C. Akanno, Tiago Valente, Mohammed Abo-Ismail, Brian Karisa, Zhiquan Wang, Graham S. Plastow. Genomic heritability and genome-wide association studies of plasma metabolites in crossbred beef cattle. (in preparation) Blood 14 +/- 2 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Blood 2-12 uM By LC-MS/MS van der Drift SGA, Houweling M, Schonewille JT, Tielens AGM, Jorritsma R: Protein and fat mobilization and associations with serum beta-hydroxybutyrate concentrations in dairy cows. J Dairy Sci. 2012 Sep;95(9):4911-4920. doi: 10.3168/jds.2011-4771. 22916895 Liver 25 +/- 5 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Longissimus Thoracis Muscle 35 +/- 8 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Milk Commercial milk, by CIL LC-MS Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Ruminal Fluid 2 +/- 1 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Semimembranosus Muscle 35 +/- 9 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Testis 19 +/- 4 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 83153 DB04151 FDB093588 92105 50599 C00052105 C01152 Methylhistidine 3741 Jain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron (1996), 52(15), 5363-70. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 BMDBP00650 Cytosolic non-specific dipeptidase Q3ZC84 CNDP2 Enzyme BMDBP02904 ATP-grasp domain-containing protein A5PJL9 Enzyme