Page last updated: 2024-12-07

histidine methyl ester

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

Description

Histidine methyl ester is a derivative of the amino acid histidine, where the carboxyl group is esterified with methanol. It is commonly used in research as a model compound for studying the properties of histidine residues in proteins. Synthesis of histidine methyl ester typically involves reacting histidine with methanol in the presence of a suitable catalyst. The compound is known to exhibit biological activity, including potential as a therapeutic agent for conditions like Alzheimer's disease. Studies on histidine methyl ester often focus on its interactions with metal ions, particularly copper and zinc, which are important in biological processes. These interactions have been explored in the context of enzyme catalysis, protein folding, and the development of novel metal-binding drugs.'

histidine methyl ester: RN given refers to (L)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

histidine methyl ester : An alpha-amino acid ester that is the methyl ester of histidine. [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 CID92893
CHEMBL ID54664
CHEBI ID169996
SCHEMBL ID262238
MeSH IDM0152391

Synonyms (41)

Synonym
9ihz1723ue ,
einecs 216-109-3
unii-9ihz1723ue
methyl (2s)-2-amino-3-(3h-imidazol-4-yl)propanoate dihydrochloride
methyl (2s)-2-amino-3-(1h-imidazol-5-yl)propanoate
CHEBI:169996
1499-46-3
7389-87-9
PVH ,
methyl l-histidinate
STK503631
histidine methyl ester
CHEMBL54664 ,
l-histidine methyl ester
bxrmewoquxoldh-lurjtmiesa-
inchi=1/c7h11n3o2/c1-12-7(11)6(8)2-5-3-9-4-10-5/h3-4,6h,2,8h2,1h3,(h,9,10)/t6-/m0/s1
BBL013268
methyl (2s)-2-amino-3-(1h-imidazol-4-yl)propanoate dihydrochloride
AKOS010395755
AKOS005171610
o-methyl-l-histidine
l-histidine, methyl ester
histidine, methyl ester, l-
histidine methyl ester, (s)-
SCHEMBL262238
(s)-methyl 2-amino-3-(1h-imidazol-5-yl)propanoate
h-his-och3
bdbm50010139
methyl 2-amino-3-(1h-imidazol-4-yl)propanoate #
mfcd08669785
methyl(2s)-2-amino-3-(1h-imidazol-5-yl)propanoate
(s)-methyl 2-amino-3-(1h-imidazol-4-yl)propanoate
methyl (2s)-2-amino-3-(1h-imidazol-4-yl)propanoate
VS-03727
DTXSID90933797
l-histidinemethyl ester
EN300-103791
(s)-methyl2-amino-3-(1h-imidazol-4-yl)propanoate
(s)-methyl histidinate
CS-0447027
E87393
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
histidine derivativeAn amino acid derivative resulting from reaction of histidine at the amino group or the carboxy group, or from the replacement of any hydrogen of histidine by a heteroatom. The definition normally excludes peptides containing alanine residues.
[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]

Pathways (1)

PathwayProteinsCompounds
histamine biosynthesis421

Protein Targets (7)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 12Homo sapiens (human)KA0.91000.24000.81921.6700AID1186310
Carbonic anhydrase 1Homo sapiens (human)KA0.02000.02001.72197.4000AID1186307
Carbonic anhydrase 2Homo sapiens (human)KA10.40000.01101.42737.8000AID1186308
Carbonic anhydrase 4Homo sapiens (human)KA23.00000.07904.45607.3000AID257047
Carbonic anhydrase 7Homo sapiens (human)KA0.88000.71003.875610.0000AID1186309
Carboxylic ester hydrolase Rattus norvegicus (Norway rat)KA0.89500.88000.89500.9100AID1186309; AID1186310
Carbonic anhydrase 14Homo sapiens (human)KA0.93000.01002.28947.2100AID1186311
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
estrous cycleCarbonic anhydrase 12Homo sapiens (human)
chloride ion homeostasisCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
bicarbonate transportCarbonic anhydrase 4Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 4Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 7Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 7Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 7Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 7Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 7Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 7Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 14Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
zinc ion bindingCarbonic anhydrase 12Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 12Homo sapiens (human)
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 4Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 4Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 4Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 7Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 14Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 14Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
membraneCarbonic anhydrase 12Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 12Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 12Homo sapiens (human)
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 4Homo sapiens (human)
rough endoplasmic reticulumCarbonic anhydrase 4Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentCarbonic anhydrase 4Homo sapiens (human)
Golgi apparatusCarbonic anhydrase 4Homo sapiens (human)
trans-Golgi networkCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
external side of plasma membraneCarbonic anhydrase 4Homo sapiens (human)
cell surfaceCarbonic anhydrase 4Homo sapiens (human)
membraneCarbonic anhydrase 4Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 4Homo sapiens (human)
transport vesicle membraneCarbonic anhydrase 4Homo sapiens (human)
secretory granule membraneCarbonic anhydrase 4Homo sapiens (human)
brush border membraneCarbonic anhydrase 4Homo sapiens (human)
perinuclear region of cytoplasmCarbonic anhydrase 4Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
cytosolCarbonic anhydrase 7Homo sapiens (human)
cytoplasmCarbonic anhydrase 7Homo sapiens (human)
plasma membraneCarbonic anhydrase 14Homo sapiens (human)
membraneCarbonic anhydrase 14Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 14Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 14Homo sapiens (human)
plasma membraneCarbonic anhydrase 14Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1186311Activation of transmembrane human carbonic anhydrase-14 incubated for 15 mins prior to testing by stopped-flow CO2 hydrase assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Mono- and di-halogenated histamine, histidine and carnosine derivatives are potent carbonic anhydrase I, II, VII, XII and XIV activators.
AID26797Partition coefficient (logP)1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
AID1186310Activation of cytosolic human carbonic anhydrase-12 incubated for 15 mins prior to testing by stopped-flow CO2 hydrase assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Mono- and di-halogenated histamine, histidine and carnosine derivatives are potent carbonic anhydrase I, II, VII, XII and XIV activators.
AID1186307Activation of cytosolic human carbonic anhydrase-1 incubated for 15 mins prior to testing by stopped-flow CO2 hydrase assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Mono- and di-halogenated histamine, histidine and carnosine derivatives are potent carbonic anhydrase I, II, VII, XII and XIV activators.
AID1133937Inhibition of histidine decarboxylase in Sprague-Dawley rat stomach assessed as decrease in 14CO2 production using L-histidine-carboxyl-14C as substrate by Dixon plot analysis1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Inhibition of histidine decarboxylase. Derivatives of histidine.
AID1186308Activation of cytosolic human carbonic anhydrase-2 incubated for 15 mins prior to testing by stopped-flow CO2 hydrase assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Mono- and di-halogenated histamine, histidine and carnosine derivatives are potent carbonic anhydrase I, II, VII, XII and XIV activators.
AID1186309Activation of cytosolic human carbonic anhydrase-7 incubated for 15 mins prior to testing by stopped-flow CO2 hydrase assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Mono- and di-halogenated histamine, histidine and carnosine derivatives are potent carbonic anhydrase I, II, VII, XII and XIV activators.
AID1133931Inhibition of histidine decarboxylase in Sprague-Dawley rat stomach assessed as decrease in 14CO2 production using L-histidine-carboxyl-14C as substrate at 0.004 mM by scintillation counting analysis1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Inhibition of histidine decarboxylase. Derivatives of histidine.
AID257047Activation constant against recombinant human CA IV isozyme by the esterase method2005Bioorganic & medicinal chemistry letters, Dec-01, Volume: 15, Issue:23
Carbonic anhydrase activators: X-ray crystal structure of the adduct of human isozyme II with L-histidine as a platform for the design of stronger activators.
AID233318Bitter threshold value1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (31.25)18.7374
1990's1 (6.25)18.2507
2000's5 (31.25)29.6817
2010's5 (31.25)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.91

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index27.91 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.94 (4.65)
Search Engine Demand Index25.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.91)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]