3-Methylhistidine

3-Methylhistidine
Names
	IUPAC name (2S)-2-amino-3-(3-methylimidazol-4-yl)propanoic acid
Identifiers
CAS Number	368-16-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	83651
ChEBI	CHEBI:27596;
ChEMBL	ChEMBL3251670;
ChemSpider	58494;
ECHA InfoCard	100.006.095
EC Number	206-704-6;
Gmelin Reference	1568650
KEGG	C01152;
PubChem CID	64969;
UNII	MEH8O8Y0H0 ;
CompTox Dashboard (EPA)	DTXSID90920521 ;
	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 pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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]

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]

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References

"3-Methylhistidine". HMDB Version 4.0. Human Metabolome Database. 20 December 2017. Retrieved 25 December 2017.
"3-Methyl-L-histidine". PubChem Compound. United States National Library of Medicine – National Center for Biotechnology Information. 23 December 2017. Retrieved 25 December 2017.
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.
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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[HMDB_3-Methylhistidine-1] "3-Methylhistidine". HMDB Version 4.0. Human Metabolome Database. 20 December 2017. Retrieved 25 December 2017.

[PubChem_-_3-Methylhistidine-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-Methylhistidine_2005_review-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.

[Muscle_protein_breakdown_and_3-Methylhistidine_2010_review-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.