Page last updated: 2024-12-07

1-methylhistidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1-methylhistidine is a derivative of the amino acid histidine, formed by methylation of the imidazole ring. It is found in muscle tissue and is a marker of muscle protein breakdown. 1-methylhistidine is produced by the breakdown of muscle protein and is excreted in urine. It is used as a marker of muscle protein breakdown in clinical research, for example, to assess the effects of malnutrition, aging, and disease. 1-methylhistidine is also used to assess the effectiveness of interventions aimed at preventing or treating muscle wasting. Studies have shown that levels of 1-methylhistidine in urine are elevated in patients with muscle wasting diseases such as cancer cachexia and sarcopenia. 1-methylhistidine is also elevated in urine after exercise, indicating an increase in muscle protein breakdown. 1-methylhistidine is an important biomarker for muscle protein turnover, and is therefore useful for monitoring muscle health in a variety of contexts.'

1-methylhistidine: found in muscle proteins; RN given refers to (L)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1-methylhistidine : A methylhistidine in which the methyl group is located at N-1. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

N(tele)-methyl-L-histidine : A L-histidine derivative in which the methyl group is at N(tele)-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID92105
CHEMBL ID1233327
CHEBI ID50599
SCHEMBL ID52216
MeSH IDM0090809

Synonyms (54)

Synonym
CHEMBL1233327 ,
l-histidine, 1-methyl-
332-80-9
1-methyl-l-histidine
1-methylhistidine
(2s)-2-amino-3-(1-methyl-1h-imidazol-4-yl)propanoic acid
n(tele)-methyl-l-histidine
pi-methylhistidine
DB04151
4-methyl-histidine
CHEBI:50599 ,
l-1-methylhistidine
1-methyl-histidine
inchi=1/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/s
n1-methyl-l-histidine
1-mhis
1 methylhistidine
1-n-methyl-l-histidine
1-methyl-l-histidine, >=98.0% (tlc)
ABB55D30-E94C-412D-9B7A-E423FA8C1620
histidine, n-tau-methyl-
BMSE000449
l-histidine, 1-methyl- (9ci)
3-(1-methylimidazol-4-yl)-l-alanine
3-methyl-l-histidine (archaic)
ntau-methyl-l-histidine
histidine, 1-methyl-, l- (8ci)
583o01bj32 ,
einecs 206-368-0
unii-583o01bj32
nsc 524367
histidine, 1-methyl-, l-
SCHEMBL52216
(s)-2-amino-3-(1-methyl-1h-imidazol-4-yl)propanoic acid
.tau.-methylhistidine
1-methyl histidine
tele-methylhistidine
AKOS016843072
FD21681
DTXSID50186848
mfcd00005295
h-his(1-me)-oh
J-019123
HY-W017006
h-his(ntau-me)-oh
Q27094989
1-methyl histidine (l-form)
CS-W017722
nt-methyl-l-histidine
AS-57334
histidine, 1-methyl-l-
bdbm50463197
n|o-methyl-l-histidine
EN300-1168703

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Selectivity of these potential biomarkers was tested by dosing rats with the cardiotoxicant isoproterenol (0."( Identification of 1- and 3-methylhistidine as biomarkers of skeletal muscle toxicity by nuclear magnetic resonance-based metabolic profiling.
Aranibar, N; Dai, J; Janovitz, EB; Lehman-McKeeman, L; Lowe-Krentz, L; Rathmacher, J; Reily, M; Robertson, D; Stryker, S; Vassallo, JD; Zhang, Y, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
zwitterionA neutral compound having formal unit electrical charges of opposite sign on non-adjacent atoms. Sometimes referred to as inner salts, dipolar ions (a misnomer).
L-histidine derivativeA proteinogenic amino acid derivative resulting from the formal reaction of L-histidine at the amino group, carboxy group, or the imidazolyl moiety, or from the replacement of any hydrogen of L-histidine by a heteroatom.
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
positive regulation of cytokine production involved in immune responseLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
negative regulation of gene expressionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of type II interferon productionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of interleukin-17 productionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of interleukin-4 productionLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
negative regulation of autophagyLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
response to muscle activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
neutral amino acid transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
isoleucine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-leucine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
methionine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
phenylalanine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
proline transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
tryptophan transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
tyrosine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
valine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
alanine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cellular response to glucose starvationLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
xenobiotic transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
response to hyperoxiaLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of glial cell proliferationLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
thyroid hormone transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cellular response to lipopolysaccharideLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid import across plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
liver regenerationLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
transport across blood-brain barrierLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-histidine transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cellular response to L-arginineLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-leucine import across plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-tryptophan transmembrane transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
negative regulation of vascular associated smooth muscle cell apoptotic processLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
positive regulation of L-leucine import across plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid transmembrane transportLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
protein bindingLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
aromatic amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
neutral L-amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-leucine transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-tryptophan transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
antiporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
thyroid hormone transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
peptide antigen bindingLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
L-amino acid transmembrane transporter activityLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
lysosomal membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
cytosolLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
basal plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
basolateral plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
apical plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
microvillus membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
intracellular membrane-bounded organelleLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
extracellular exosomeLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
external side of apical plasma membraneLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
amino acid transport complexLarge neutral amino acids transporter small subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1588255Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inhibition of [3H]-gabapentin uptake preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting analysis r2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
l-Type amino acid transporter 1 activity of 1,2,3-triazolyl analogs of l-histidine and l-tryptophan.
AID1398361Trans-stimulation of human LAT1 expressed in TREx HEK293 cells assessed as induction of [3H]-gabapentin efflux at 200 uM after 3 mins by scintillation counting analysis relative to L-phenylalanine2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1).
AID1133933Inhibition of histidine decarboxylase in Sprague-Dawley rat stomach assessed as decrease in 14CO2 production using L-histidine-carboxyl-14C as substrate at 0.10 mM by scintillation counting analysis1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Inhibition of histidine decarboxylase. Derivatives of histidine.
AID1398359Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inhibition of [3H]-gabapentin uptake preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting analysis r2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1).
AID1588256Cis-inhibition of human LAT1 expressed in TREx HEK293 cells assessed as inhibition of [3H]-gabapentin uptake preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting analysis2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
l-Type amino acid transporter 1 activity of 1,2,3-triazolyl analogs of l-histidine and l-tryptophan.
AID1398360Cis-inhibition of human LAT1 expressed in TREx HEK293 cells at 200 uM assessed as inhibition of [3H]-gabapentin uptake at 200 uM preincubated for 3 mins at 37 degC followed by washing with choline buffer and measured after 3 hrs by scintillation counting 2018Journal of medicinal chemistry, 08-23, Volume: 61, Issue:16
Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1).
AID1588254Trans-stimulation of human LAT1 expressed in TREx HEK293 cells assessed as induction of [3H]-gabapentin efflux at 200 uM after 3 mins by scintillation counting analysis relative to L-phenylalanine2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
l-Type amino acid transporter 1 activity of 1,2,3-triazolyl analogs of l-histidine and l-tryptophan.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (59)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (47.46)18.7374
1990's4 (6.78)18.2507
2000's4 (6.78)29.6817
2010's19 (32.20)24.3611
2020's4 (6.78)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.33

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index35.33 (24.57)
Research Supply Index4.19 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index44.79 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (4.84%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (1.61%)4.05%
Observational0 (0.00%)0.25%
Other58 (93.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]