3-Methylhistidine

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]

3-Methylhistidine
Names
Preferred IUPAC name
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 83651
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.095
EC Number
  • 206-704-6
Gmelin Reference
 1568650
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
    Key: JDHILDINMRGULE-LURJTMIESA-N
SMILES
  • CN1C=NC=C1CC(C(=O)O)N
Properties
Chemical formula
 C7H11N3O2
Molar mass 169.184
Solubility in water
 200 mg/mL at 25 °C[1][2]
Hazards
GHS labelling:
Pictograms
Signal word
 Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 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).
Infobox references

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 3.63–69.27 micromoles per millimole (μmol/mmol) of creatinine, with most studies reporting the average urinary concentration between 15–20 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 0.0–5.9 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 1.39–6.25 μM.[1]

References
  1. "3-Methylhistidine". HMDB Version 4.0. Human Metabolome Database. 20 December 2017. Retrieved 25 December 2017.
  2. "3-Methyl-L-histidine". PubChem Compound. United States National Library of Medicine – National Center for Biotechnology Information. 23 December 2017. Retrieved 25 December 2017.
  3. Chinkes DL (September 2005). "Methods for measuring tissue protein breakdown rate in vivo". Current Opinion in Clinical Nutrition and Metabolic Care. 8 (5): 534–537. doi:10.1097/01.mco.0000170754.25372.37. PMID 16079625. S2CID 8318490.
  4. Holm L, Kjaer M (September 2010). "Measuring protein breakdown rate in individual proteins in vivo". Current Opinion in Clinical Nutrition and Metabolic Care. 13 (5): 526–531. doi:10.1097/MCO.0b013e32833c3c64. PMC 3008417. PMID 20616712.
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