1-METHYLHISTIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C7H11N3O2
Molecular Weight	169.1811
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C=NC(C[C@H](N)C(O)=O)=C1

InChI

InChIKey=BRMWTNUJHUMWMS-LURJTMIESA-N

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

HIDE SMILES / InChI

Molecular Formula	C7H11N3O2
Molecular Weight	169.1811
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Quantification of histidine, 1-methylhistidine and 3-methylhistidine in plasma and urine by capillary electrophoresis UV-detection.	2010-12	20886517
Characteristic metabolism of free amino acids in cetacean plasma: cluster analysis and comparison with mice.	2010-11-02	21072195
Microwave-accelerated derivatization for capillary electrophoresis with laser-induced fluorescence detection: a case study for determination of histidine, 1- and 3-methylhistidine in human urine.	2010-06-30	20685438
Biomarkers of meat intake and the application of nutrigenomics.	2010-02	20374789
Effects of feeding hexane-extracts of a shochu distillery by-product on skeletal muscle protein degradation in broiler chicken.	2010	20057147
Effects of rapid or slow body mass reduction on body composition in adult rats.	2009-09	19794927
[Metabonomic variation of esophageal cancer within different ethnic groups in Xinjiang, China].	2009-07	19954070
Prediction of breast cancer by profiling of urinary RNA metabolites using Support Vector Machine-based feature selection.	2009-04-05	19344524
Application of 1H NMR-based metabonomics in the study of metabolic profiling of human hepatocellular carcinoma and liver cirrhosis.	2009-04	19469021
A rapid MEKC method for the simultaneous determination of creatinine, 1- and 3-methylhistidine in human urine.	2009-02	19156770
Effects of orally administered glycine on myofibrillar proteolysis and expression of proteolytic-related genes of skeletal muscle in chicks.	2008-08	17624491
'Systems toxicology' approach identifies coordinated metabolic responses to copper in a terrestrial non-model invertebrate, the earthworm Lumbricus rubellus.	2008-06-03	18522721
O2 binding to human serum albumin incorporating iron porphyrin with a covalently linked methyl-L-histidine isomer.	2008-03	18205324
Suppression of myofibrillar proteolysis in chick skeletal muscles by alpha-ketoisocaproate.	2007-09	16998714
AMPK activation stimulates myofibrillar protein degradation and expression of atrophy-related ubiquitin ligases by increasing FOXO transcription factors in C2C12 myotubes.	2007-07	17617726
Determination of 1-methylhistidine and 3-methylhistidine by capillary and chip electrophoresis with contactless conductivity detection.	2007-07	17557358
Effects of orally administrated amino acids on myofibrillar proteolysis in chicks.	2006-08	16926512
Determination of free amino acids and related compounds in amniotic fluid by capillary electrophoresis with contactless conductivity detection.	2006-07-24	16412708
Leucine suppresses myofibrillar proteolysis by down-regulating ubiquitin-proteasome pathway in chick skeletal muscles.	2005-10-21	16153608
Effects of fasting and refeeding on expression of proteolytic-related genes in skeletal muscle of chicks.	2005-08	16261996
Determination of 3-methylhistidine and 1-methylhistidine in untreated urine samples by capillary electrophoresis.	2005-07-05	15899597
Design of a five-coordinate heme protein maquette: a spectroscopic model of deoxymyoglobin.	2004-12-27	15606161
Protein utilisation and turnover in lines of chickens selected for different aspects of body composition.	2004-12	15697017
Environmental metabonomics: applying combination biomarker analysis in earthworms at a metal contaminated site.	2004-11	15736850
Cysteine suppresses oxidative stress-induced myofibrillar proteolysis in chick myotubes.	2004-11	15564672
Myofibrillar proteolysis in chick myotubes during oxidative stress.	2004-02	15228217
Effects of serum deprivation on myofibrillar proteolysis in chick myotube cultures.	2003-11	14646208
Triiodothyronine but not thyroxine accelerates myofibrillar proteolysis via ATP production in cultured muscle cells.	2003-11	14646207
Effects of corticosterone on Ca2+ uptake and myofibrillar disassembly in primary muscle cell culture.	2003-02	12728981
Ultraviolet spectrophotometric characterization of copper(II) complexes with imidazole N-methyl derivatives of L-histidine in aqueous solution.	2003-01-01	12509160
Effects of the thyroid hormone on differentiation, growth, and proteolysis in cultured muscle cells during serum deprivation.	2002-08	12489816
Effect of different dietary protein composition on skeletal muscle atrophy by suspension hypokinesia/hypodynamia in rats.	2002-04	12171431
Increase of gamma-glutamyl-beta-alanyl-histidine isopeptide in the macromolecular fraction of model chicken extract during heating and distribution in commercial chicken extracts.	2002-04	11989761
Ntau-methylhistidine excretion is a valid index of myofibrillar protein breakdown in the guineapig (Cavia porcellus).	2001-10	11669322
Urinary 1-methylhistidine is a marker of meat consumption in Black and in White California Seventh-day Adventists.	2000-10-15	11052553
Metabolic effects of a protein-supplemented carbohydrate drink in marathon runners.	1999-06	10362454
Hormonal regulation of protein metabolism in relation to nutrition and disease.	1998-02	9478024
High-performance liquid chromatographic determination of imidazole dipeptides, histidine, 1-methylhistidine and 3-methylhistidine in equine and camel muscle and individual muscle fibres.	1997-01-10	9029312
750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma.	1995-03-01	7762816
High-performance liquid chromatography-electrochemical detection of 3-methylhistidine in human urine.	1992-12-23	1484110
Basic amino acid in the pathogenesis of caries.	1991	1819935
Protein and amino acid metabolism during early starvation as reflected by excretion of urea and methylhistidines.	1989-12	2593832
Evaluation of urinary 3-methylhistidine excretion in infection by measurements of 1-methylhistidine and the creatinine ratios.	1989-01	2912013
Increased excretion of urea and N tau -methylhistidine by rats and humans after a bout of exercise.	1982-01	7061274
ISOLATION OF 3-METHYL HISTIDINE FROM WHALEMEAT EXTRACT AND THE PREPARATION OF SOME DERIVATIVES.	1964-04-11	14156296

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:29:20 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:20 GMT 2025`
Record UNII	583O01BJ32
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1-METHYLHISTIDINE

Systematic Name

English

NSC-524367

Preferred Name

English

1-N-METHYL-L-HISTIDINE

Systematic Name

English

.TAU.-METHYLHISTIDINE

Common Name

English

L-HISTIDINE, 1-METHYL-

Systematic Name

English

1-METHYL HISTIDINE

Systematic Name

English

HISTIDINE, 1-METHYL-, L-

Systematic Name

English

1-METHYL-L-HISTIDINE

Systematic Name

English

N1-METHYL-L-HISTIDINE

Systematic Name

English

TELE-METHYLHISTIDINE

Common Name

English

(S)-2-AMINO-3-(1-METHYL-1H-IMIDAZOL-4-YL)PROPANOIC ACID

Systematic Name

English

Classification Tree Code System Code

LOINC

13406-4