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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:07:14 UTC |
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Update Date | 2020-06-04 20:10:20 UTC |
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BMDB ID | BMDB0000001 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1-Methylhistidine |
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Description | 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. |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid | ChEBI | (2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoate | Generator | 1 Methylhistidine | HMDB | 1-Methyl histidine | HMDB | 1-Methyl-histidine | HMDB | 1-Methyl-L-histidine | HMDB | 1-MHis | HMDB | 1-N-Methyl-L-histidine | HMDB | L-1-Methylhistidine | HMDB | N1-Methyl-L-histidine | HMDB | 1-Methylhistidine dihydrochloride | HMDB | 1-Methylhistidine | ChEBI | Tau methylhistidine | HMDB | N(Tau)-methylhistidine | HMDB | Tau-methyl-L-histidine | HMDB | N Tau-methylhistidine | HMDB |
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Chemical Formula | C7H11N3O2 |
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Average Molecular Weight | 169.1811 |
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Monoisotopic Molecular Weight | 169.085126611 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 332-80-9 |
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SMILES | Not Available |
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InChI Identifier | 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 |
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InChI Key | BRMWTNUJHUMWMS-LURJTMIESA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Histidine and derivatives |
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Alternative Parents | |
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Substituents | - Histidine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Imidazolyl carboxylic acid derivative
- Aralkylamine
- N-substituted imidazole
- Azole
- Imidazole
- Heteroaromatic compound
- Amino acid
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 249 | http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Milk
- Placenta
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 14 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 2-12 uM | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 25 +/- 5 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 35 +/- 8 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 2 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 35 +/- 9 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 19 +/- 4 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details |
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External Links |
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HMDB ID | HMDB0000001 |
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DrugBank ID | DB04151 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB093588 |
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KNApSAcK ID | C00052105 |
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Chemspider ID | 83153 |
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KEGG Compound ID | C01152 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Methylhistidine |
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METLIN ID | 3741 |
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PubChem Compound | 92105 |
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PDB ID | Not Available |
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ChEBI ID | 50599 |
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References |
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Synthesis Reference | Jain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron (1996), 52(15), 5363-70. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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. [PubMed:28306241 ]
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