3-Methylhistidine
Chemical compound
From Wikipedia, the free encyclopedia
3-Methylhistidine (3-MH) is a post-translationally modified amino acid which is excreted in human urine.[1][2] Urinary concentration of 3-methylhistidine is a biomarker for skeletal muscle protein breakdown in humans who have been subject to muscle injury.[1][3][4] Urinary 3-methylhistidine concentrations are also elevated from consumption of soy-based products and meat, particularly chicken.[1]
-2-amino-3-(3-methylimidazol-4-yl)propanoic_acid.svg)
| |
| Names | |
|---|---|
| Systematic IUPAC name
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid | |
| Identifiers | |
3D model (JSmol) |
|
| 83651 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.095 |
| EC Number |
|
| 1568650 | |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C7H11N3O2 | |
| Molar mass | 169.184 |
| 200 mg/mL at 25 °C[1][2] | |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Biochemistry
3-Methylhistidine is a metabolic product that is produced in the body via the enzymatic methylation of histidine during peptide bond synthesis and the methylation of actin and myosin.[1][2]
Detection in body fluids
The normal concentration of 3-methylhistidine in the urine of healthy adult humans has been detected and quantified in a range of 3.63â69.27 micromoles per millimole (μmol/mmol) of creatinine, with most studies reporting the average urinary concentration between 15 and 20 μmol/mmol of creatinine.[1] The average concentration of 3-methylhistidine in human blood plasma has been detected and quantified at 2.85 micromolar (μM) with a range of 0.0â5.9 μM.[1] The average concentration of 3-methylhistidine in human cerebrospinal fluid (CSF) has been detected and quantified at 3.82 μM with a range of 1.39â6.25 μM.[1]