Compounds > delta-n-methylarginine
Page last updated: 2024-11-08

delta-n-methylarginine

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Description

N(5)-methyl-L-arginine : A non-proteinogenic L-alpha-amino acid that is L-arginine substituted by a methyl group at N(5)-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 CID173566
CHEMBL ID99636
CHEBI ID21848
SCHEMBL ID2307076
MeSH IDM0089903

Synonyms (16)

Synonym
bdbm50049254
delta-n-methylarginine
n(5)-methyl-l-arginine
(2s)-2-amino-5-(n-methylcarbamimidamido)pentanoic acid
77044-73-6
n(5)-carbamimidoyl-n(5)-methyl-l-ornithine
CHEBI:21848 ,
CHEMBL99636 ,
(2s)-2-amino-5-[carbamimidoyl(methyl)amino]pentanoic acid
l-ornithine, n(5)-(aminoiminomethyl)-n(5)-methyl-
DTXSID70227848
n'-monomethyl-l-arginine
SCHEMBL2307076
6-monomethyl-l-arginine
Q27109412
PD178384
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
guanidinesAny organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
L-arginine derivativeA proteinogenic amino acid derivative resulting from reaction of L-arginine at the amino group, the carboxy group, or the guanidyl group, or from the replacement of any hydrogen of L-arginine by a heteroatom.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)IC50 (µMol)5,000.00007.80008.25708.7140AID326381
Nitric oxide synthase, endothelialHomo sapiens (human)IC50 (µMol)5,002.95000.07202.58738.7000AID326377; AID68136
Nitric oxide synthase, brainHomo sapiens (human)IC50 (µMol)5,005.00000.03502.711910.0000AID146117; AID326379
Nitric oxide synthase, inducibleMus musculus (house mouse)IC50 (µMol)25.00000.00103.39119.6000AID143404
Nitric oxide synthase, inducibleHomo sapiens (human)IC50 (µMol)5,007.00000.00022.319010.0000AID326378; AID92005
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (96)

Processvia Protein(s)Taxonomy
citrulline metabolic processN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
regulation of systemic arterial blood pressureN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
arginine catabolic processN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
nitric oxide mediated signal transductionN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
negative regulation of cell population proliferationN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
negative regulation of vascular permeabilityN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
positive regulation of angiogenesisN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
nitric oxide metabolic processN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
negative regulation of cellular response to hypoxiaN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
arginine metabolic processN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
positive regulation of gene expressionNitric oxide synthase, endothelialHomo sapiens (human)
angiogenesisNitric oxide synthase, endothelialHomo sapiens (human)
ovulation from ovarian follicleNitric oxide synthase, endothelialHomo sapiens (human)
in utero embryonic developmentNitric oxide synthase, endothelialHomo sapiens (human)
blood vessel remodelingNitric oxide synthase, endothelialHomo sapiens (human)
regulation of sodium ion transportNitric oxide synthase, endothelialHomo sapiens (human)
regulation of the force of heart contraction by chemical signalNitric oxide synthase, endothelialHomo sapiens (human)
regulation of systemic arterial blood pressure by endothelinNitric oxide synthase, endothelialHomo sapiens (human)
aortic valve morphogenesisNitric oxide synthase, endothelialHomo sapiens (human)
pulmonary valve morphogenesisNitric oxide synthase, endothelialHomo sapiens (human)
endocardial cushion morphogenesisNitric oxide synthase, endothelialHomo sapiens (human)
arginine catabolic processNitric oxide synthase, endothelialHomo sapiens (human)
nitric oxide biosynthetic processNitric oxide synthase, endothelialHomo sapiens (human)
potassium ion transportNitric oxide synthase, endothelialHomo sapiens (human)
calcium ion transportNitric oxide synthase, endothelialHomo sapiens (human)
mitochondrion organizationNitric oxide synthase, endothelialHomo sapiens (human)
regulation of blood pressureNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of cell population proliferationNitric oxide synthase, endothelialHomo sapiens (human)
response to heatNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of platelet activationNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of muscle hyperplasiaNitric oxide synthase, endothelialHomo sapiens (human)
smooth muscle hyperplasiaNitric oxide synthase, endothelialHomo sapiens (human)
removal of superoxide radicalsNitric oxide synthase, endothelialHomo sapiens (human)
lung developmentNitric oxide synthase, endothelialHomo sapiens (human)
positive regulation of guanylate cyclase activityNitric oxide synthase, endothelialHomo sapiens (human)
regulation of nervous system processNitric oxide synthase, endothelialHomo sapiens (human)
lipopolysaccharide-mediated signaling pathwayNitric oxide synthase, endothelialHomo sapiens (human)
response to fluid shear stressNitric oxide synthase, endothelialHomo sapiens (human)
vasodilationNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of potassium ion transportNitric oxide synthase, endothelialHomo sapiens (human)
positive regulation of blood vessel endothelial cell migrationNitric oxide synthase, endothelialHomo sapiens (human)
endothelial cell migrationNitric oxide synthase, endothelialHomo sapiens (human)
cell redox homeostasisNitric oxide synthase, endothelialHomo sapiens (human)
positive regulation of Notch signaling pathwayNitric oxide synthase, endothelialHomo sapiens (human)
positive regulation of angiogenesisNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of smooth muscle cell proliferationNitric oxide synthase, endothelialHomo sapiens (human)
homeostasis of number of cells within a tissueNitric oxide synthase, endothelialHomo sapiens (human)
establishment of localization in cellNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of calcium ion transportNitric oxide synthase, endothelialHomo sapiens (human)
ventricular septum morphogenesisNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of biomineral tissue developmentNitric oxide synthase, endothelialHomo sapiens (human)
blood vessel diameter maintenanceNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway via death domain receptorsNitric oxide synthase, endothelialHomo sapiens (human)
nitric oxide mediated signal transductionNitric oxide synthase, endothelialHomo sapiens (human)
response to hormoneNitric oxide synthase, endothelialHomo sapiens (human)
negative regulation of blood pressureNitric oxide synthase, endothelialHomo sapiens (human)
response to lipopolysaccharideNitric oxide synthase, endothelialHomo sapiens (human)
response to hypoxiaNitric oxide synthase, brainHomo sapiens (human)
regulation of sodium ion transportNitric oxide synthase, brainHomo sapiens (human)
arginine catabolic processNitric oxide synthase, brainHomo sapiens (human)
nitric oxide biosynthetic processNitric oxide synthase, brainHomo sapiens (human)
striated muscle contractionNitric oxide synthase, brainHomo sapiens (human)
myoblast fusionNitric oxide synthase, brainHomo sapiens (human)
response to heatNitric oxide synthase, brainHomo sapiens (human)
negative regulation of calcium ion transport into cytosolNitric oxide synthase, brainHomo sapiens (human)
regulation of cardiac muscle contraction by calcium ion signalingNitric oxide synthase, brainHomo sapiens (human)
peptidyl-cysteine S-nitrosylationNitric oxide synthase, brainHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationNitric oxide synthase, brainHomo sapiens (human)
multicellular organismal response to stressNitric oxide synthase, brainHomo sapiens (human)
xenobiotic catabolic processNitric oxide synthase, brainHomo sapiens (human)
vasodilationNitric oxide synthase, brainHomo sapiens (human)
negative regulation of potassium ion transportNitric oxide synthase, brainHomo sapiens (human)
cell redox homeostasisNitric oxide synthase, brainHomo sapiens (human)
positive regulation of DNA-templated transcriptionNitric oxide synthase, brainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IINitric oxide synthase, brainHomo sapiens (human)
negative regulation of hydrolase activityNitric oxide synthase, brainHomo sapiens (human)
negative regulation of serotonin uptakeNitric oxide synthase, brainHomo sapiens (human)
negative regulation of calcium ion transportNitric oxide synthase, brainHomo sapiens (human)
regulation of cardiac muscle contractionNitric oxide synthase, brainHomo sapiens (human)
regulation of ryanodine-sensitive calcium-release channel activityNitric oxide synthase, brainHomo sapiens (human)
cellular response to growth factor stimulusNitric oxide synthase, brainHomo sapiens (human)
positive regulation of the force of heart contractionNitric oxide synthase, brainHomo sapiens (human)
positive regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwayNitric oxide synthase, brainHomo sapiens (human)
positive regulation of sodium ion transmembrane transportNitric oxide synthase, brainHomo sapiens (human)
regulation of calcium ion transmembrane transport via high voltage-gated calcium channelNitric oxide synthase, brainHomo sapiens (human)
positive regulation of membrane repolarization during ventricular cardiac muscle cell action potentialNitric oxide synthase, brainHomo sapiens (human)
positive regulation of guanylate cyclase activityNitric oxide synthase, brainHomo sapiens (human)
nitric oxide mediated signal transductionNitric oxide synthase, brainHomo sapiens (human)
response to hormoneNitric oxide synthase, brainHomo sapiens (human)
negative regulation of blood pressureNitric oxide synthase, brainHomo sapiens (human)
response to lipopolysaccharideNitric oxide synthase, brainHomo sapiens (human)
response to hypoxiaNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of leukocyte mediated cytotoxicityNitric oxide synthase, inducibleHomo sapiens (human)
innate immune response in mucosaNitric oxide synthase, inducibleHomo sapiens (human)
arginine catabolic processNitric oxide synthase, inducibleHomo sapiens (human)
superoxide metabolic processNitric oxide synthase, inducibleHomo sapiens (human)
nitric oxide biosynthetic processNitric oxide synthase, inducibleHomo sapiens (human)
circadian rhythmNitric oxide synthase, inducibleHomo sapiens (human)
response to bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of gene expressionNitric oxide synthase, inducibleHomo sapiens (human)
peptidyl-cysteine S-nitrosylationNitric oxide synthase, inducibleHomo sapiens (human)
prostaglandin secretionNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of interleukin-6 productionNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of interleukin-8 productionNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cell population proliferationNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of protein catabolic processNitric oxide synthase, inducibleHomo sapiens (human)
defense response to bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cellular respirationNitric oxide synthase, inducibleHomo sapiens (human)
cell redox homeostasisNitric oxide synthase, inducibleHomo sapiens (human)
regulation of insulin secretionNitric oxide synthase, inducibleHomo sapiens (human)
defense response to Gram-negative bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of killing of cells of another organismNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to lipopolysaccharideNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to type II interferonNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to xenobiotic stimulusNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cytokine production involved in inflammatory responseNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of blood pressureNitric oxide synthase, inducibleHomo sapiens (human)
response to hormoneNitric oxide synthase, inducibleHomo sapiens (human)
nitric oxide mediated signal transductionNitric oxide synthase, inducibleHomo sapiens (human)
response to lipopolysaccharideNitric oxide synthase, inducibleHomo sapiens (human)
inflammatory responseNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of guanylate cyclase activityNitric oxide synthase, inducibleHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (21)

Processvia Protein(s)Taxonomy
catalytic activityN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
dimethylargininase activityN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
metal ion bindingN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
amino acid bindingN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
actin monomer bindingNitric oxide synthase, endothelialHomo sapiens (human)
nitric-oxide synthase activityNitric oxide synthase, endothelialHomo sapiens (human)
protein bindingNitric oxide synthase, endothelialHomo sapiens (human)
calmodulin bindingNitric oxide synthase, endothelialHomo sapiens (human)
FMN bindingNitric oxide synthase, endothelialHomo sapiens (human)
heme bindingNitric oxide synthase, endothelialHomo sapiens (human)
tetrahydrobiopterin bindingNitric oxide synthase, endothelialHomo sapiens (human)
arginine bindingNitric oxide synthase, endothelialHomo sapiens (human)
cadmium ion bindingNitric oxide synthase, endothelialHomo sapiens (human)
flavin adenine dinucleotide bindingNitric oxide synthase, endothelialHomo sapiens (human)
NADP bindingNitric oxide synthase, endothelialHomo sapiens (human)
scaffold protein bindingNitric oxide synthase, endothelialHomo sapiens (human)
nitric-oxide synthase activityNitric oxide synthase, brainHomo sapiens (human)
calcium channel regulator activityNitric oxide synthase, brainHomo sapiens (human)
protein bindingNitric oxide synthase, brainHomo sapiens (human)
calmodulin bindingNitric oxide synthase, brainHomo sapiens (human)
FMN bindingNitric oxide synthase, brainHomo sapiens (human)
sodium channel regulator activityNitric oxide synthase, brainHomo sapiens (human)
heme bindingNitric oxide synthase, brainHomo sapiens (human)
tetrahydrobiopterin bindingNitric oxide synthase, brainHomo sapiens (human)
arginine bindingNitric oxide synthase, brainHomo sapiens (human)
transmembrane transporter bindingNitric oxide synthase, brainHomo sapiens (human)
cadmium ion bindingNitric oxide synthase, brainHomo sapiens (human)
calcium-dependent protein bindingNitric oxide synthase, brainHomo sapiens (human)
flavin adenine dinucleotide bindingNitric oxide synthase, brainHomo sapiens (human)
NADP bindingNitric oxide synthase, brainHomo sapiens (human)
scaffold protein bindingNitric oxide synthase, brainHomo sapiens (human)
nitric-oxide synthase activityNitric oxide synthase, inducibleHomo sapiens (human)
protein bindingNitric oxide synthase, inducibleHomo sapiens (human)
calmodulin bindingNitric oxide synthase, inducibleHomo sapiens (human)
FMN bindingNitric oxide synthase, inducibleHomo sapiens (human)
heme bindingNitric oxide synthase, inducibleHomo sapiens (human)
tetrahydrobiopterin bindingNitric oxide synthase, inducibleHomo sapiens (human)
arginine bindingNitric oxide synthase, inducibleHomo sapiens (human)
protein homodimerization activityNitric oxide synthase, inducibleHomo sapiens (human)
metal ion bindingNitric oxide synthase, inducibleHomo sapiens (human)
flavin adenine dinucleotide bindingNitric oxide synthase, inducibleHomo sapiens (human)
NADP bindingNitric oxide synthase, inducibleHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (25)

Processvia Protein(s)Taxonomy
cytosolN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
extracellular exosomeN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
Golgi membraneNitric oxide synthase, endothelialHomo sapiens (human)
nucleusNitric oxide synthase, endothelialHomo sapiens (human)
cytoplasmNitric oxide synthase, endothelialHomo sapiens (human)
Golgi apparatusNitric oxide synthase, endothelialHomo sapiens (human)
cytosolNitric oxide synthase, endothelialHomo sapiens (human)
cytoskeletonNitric oxide synthase, endothelialHomo sapiens (human)
plasma membraneNitric oxide synthase, endothelialHomo sapiens (human)
caveolaNitric oxide synthase, endothelialHomo sapiens (human)
endocytic vesicle membraneNitric oxide synthase, endothelialHomo sapiens (human)
nucleusNitric oxide synthase, endothelialHomo sapiens (human)
plasma membraneNitric oxide synthase, endothelialHomo sapiens (human)
cytosolNitric oxide synthase, endothelialHomo sapiens (human)
photoreceptor inner segmentNitric oxide synthase, brainHomo sapiens (human)
nucleoplasmNitric oxide synthase, brainHomo sapiens (human)
cytoplasmNitric oxide synthase, brainHomo sapiens (human)
mitochondrionNitric oxide synthase, brainHomo sapiens (human)
cytosolNitric oxide synthase, brainHomo sapiens (human)
cytoskeletonNitric oxide synthase, brainHomo sapiens (human)
plasma membraneNitric oxide synthase, brainHomo sapiens (human)
sarcoplasmic reticulumNitric oxide synthase, brainHomo sapiens (human)
sarcolemmaNitric oxide synthase, brainHomo sapiens (human)
dendritic spineNitric oxide synthase, brainHomo sapiens (human)
membrane raftNitric oxide synthase, brainHomo sapiens (human)
synapseNitric oxide synthase, brainHomo sapiens (human)
perinuclear region of cytoplasmNitric oxide synthase, brainHomo sapiens (human)
cell peripheryNitric oxide synthase, brainHomo sapiens (human)
protein-containing complexNitric oxide synthase, brainHomo sapiens (human)
plasma membraneNitric oxide synthase, brainHomo sapiens (human)
postsynaptic densityNitric oxide synthase, brainHomo sapiens (human)
cytosolNitric oxide synthase, brainHomo sapiens (human)
nucleusNitric oxide synthase, brainHomo sapiens (human)
nucleusNitric oxide synthase, inducibleHomo sapiens (human)
nucleoplasmNitric oxide synthase, inducibleHomo sapiens (human)
cytoplasmNitric oxide synthase, inducibleHomo sapiens (human)
peroxisomeNitric oxide synthase, inducibleHomo sapiens (human)
peroxisomal matrixNitric oxide synthase, inducibleHomo sapiens (human)
cytosolNitric oxide synthase, inducibleHomo sapiens (human)
cortical cytoskeletonNitric oxide synthase, inducibleHomo sapiens (human)
perinuclear region of cytoplasmNitric oxide synthase, inducibleHomo sapiens (human)
plasma membraneNitric oxide synthase, inducibleHomo sapiens (human)
nucleusNitric oxide synthase, inducibleHomo sapiens (human)
cytosolNitric oxide synthase, inducibleHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID143404Compound was evaluated for inhibitory activity against iNOS obtained from RAW 264.7 cells.1998Bioorganic & medicinal chemistry letters, Nov-03, Volume: 8, Issue:21
Conformationally constrained NO synthase inhibitors: rigid analogs of L-N-iminoethylornithine.
AID92300In vivo inhibition of inducible Nitric oxide Synthase ( iNOS) in anesthetized rats at concentration of 10 uM1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Synthesis of L-thiocitrulline, L-homothiocitrulline, and S-methyl-L-thiocitrulline: a new class of potent nitric oxide synthase inhibitors.
AID68136Inhibitory activity against human Endothelial nitric oxide synthase1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
2-Iminopiperidine and other 2-iminoazaheterocycles as potent inhibitors of human nitric oxide synthase isoforms.
AID92301In vivo inhibition of inducible Nitric oxide Synthase ( iNOS) in anesthetized rats at concentration of 100 uM1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Synthesis of L-thiocitrulline, L-homothiocitrulline, and S-methyl-L-thiocitrulline: a new class of potent nitric oxide synthase inhibitors.
AID326378Inhibition of human recombinant iNOS by griess assay2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
N(delta)-Methylated L-arginine derivatives and their effects on the nitric oxide generating system.
AID146271In vivo inhibition of brain tissue Nitric oxide Synthase ( bNOS) in anesthetized rats at concentration of 10 uM1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Synthesis of L-thiocitrulline, L-homothiocitrulline, and S-methyl-L-thiocitrulline: a new class of potent nitric oxide synthase inhibitors.
AID146272In vivo inhibition of brain tissue Nitric oxide Synthase ( bNOS) in anesthetized rats at concentration of 100 uM1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Synthesis of L-thiocitrulline, L-homothiocitrulline, and S-methyl-L-thiocitrulline: a new class of potent nitric oxide synthase inhibitors.
AID92005Inhibitory activity against human inducible nitric oxide synthase1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
2-Iminopiperidine and other 2-iminoazaheterocycles as potent inhibitors of human nitric oxide synthase isoforms.
AID146117Inhibitory activity against human Neuronal nitric oxide synthase1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
2-Iminopiperidine and other 2-iminoazaheterocycles as potent inhibitors of human nitric oxide synthase isoforms.
AID234272Selectivity is defined as the ratio of the IC50(hncNOS) to IC50(hiNOS)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
2-Iminopiperidine and other 2-iminoazaheterocycles as potent inhibitors of human nitric oxide synthase isoforms.
AID326379Inhibition of human recombinant nNOS by griess assay2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
N(delta)-Methylated L-arginine derivatives and their effects on the nitric oxide generating system.
AID326383Metabolic stability in pig liver microsomes per mg protein at pH 6.32008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
N(delta)-Methylated L-arginine derivatives and their effects on the nitric oxide generating system.
AID234271Selectivity is defined as the ratio of the IC50(hecNOS) to IC50(hiNOS)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
2-Iminopiperidine and other 2-iminoazaheterocycles as potent inhibitors of human nitric oxide synthase isoforms.
AID326381Inhibition of human recombinant DDAH1 expressed in Escherichia coli BL21 cells2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
N(delta)-Methylated L-arginine derivatives and their effects on the nitric oxide generating system.
AID326377Inhibition of human recombinant eNOS by griess assay2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
N(delta)-Methylated L-arginine derivatives and their effects on the nitric oxide generating system.
AID326382Metabolic stability in pig liver mitochondria per mg protein at pH 6.32008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
N(delta)-Methylated L-arginine derivatives and their effects on the nitric oxide generating system.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (10.00)18.7374
1990's7 (70.00)18.2507
2000's2 (20.00)29.6817
2010's0 (0.00)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: 12.67

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

MetricThis Compound (vs All)
Research Demand Index12.67 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index5.07 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.67)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbon monoxide
Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.		210carbon oxide;
gas molecular entity;
one-carbon compound		biomarker;
EC 1.9.3.1 (cytochrome c oxidase) inhibitor;
human metabolite;
ligand;
metabolite;
mitochondrial respiratory-chain inhibitor;
mouse metabolite;
neurotoxin;
neurotransmitter;
P450 inhibitor;
probe;
signalling molecule;
vasodilator agent
pimagedine
pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.		1.9910guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor
s-methylisothiopseudouronium
S-methylisothiopseudouronium: inhibits nitric oxide synthase; structure in first source		1.9510
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		210antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
ornithine
Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.		2.3920non-proteinogenic L-alpha-amino acid;
ornithine		algal metabolite;
hepatoprotective agent;
mouse metabolite
dinitrofluorobenzene
Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.		1.9910C-nitro compound;
organofluorine compound		agrochemical;
allergen;
chromatographic reagent;
EC 2.7.3.2 (creatine kinase) inhibitor;
protein-sequencing agent;
spectrophotometric reagent
arginine
Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.		8.3870arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
citrulline
citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.		2.0410amino acid zwitterion;
citrulline		Daphnia magna metabolite;
EC 1.14.13.39 (nitric oxide synthase) inhibitor;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
protective agent;
Saccharomyces cerevisiae metabolite
tetradecanoylphorbol acetate
Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.		210acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator
isothiuronium
Isothiuronium: An undecenyl THIOUREA which may have topical anti-inflammatory activity.		1.9510
s-methylthiocitrulline
S-methylthiocitrulline: a nitric oxide synthase inhibitor; structure in first source. S-methyl-L-thiocitrulline : An L-arginine derivative in which the guanidino NH2 group of L-arginine is replaced by a methylsufanyl group.		1.9810imidothiocarbamic ester;
L-arginine derivative;
L-ornithine derivative;
non-proteinogenic L-alpha-amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
neuroprotective agent
n(g)-iminoethylornithine
[no description available]		1.9910L-alpha-amino acid
n(omega)-hydroxyarginine
N(omega)-hydroxyarginine: can cause vasorelaxation of bovine intrapulmonary artery; structure given in first source. N(5)-[(Z)-amino(hydroxyimino)methyl]-L-ornithine : An N(5)-[amino(hydroxyimino)methyl]-L-ornithine in which the double bond has Z-configuration.		2.4420amino acid zwitterion;
N(5)-[(E)-amino(hydroxyimino)methyl]ornithine;
N(5)-[(hydroxyamino)(imino)methyl]ornithine;
N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine;
N(5)-[amino(hydroxyimino)methyl]-L-ornithine;
N(5)-[amino(hydroxyimino)methyl]ornithine;
N(omega)-hydroxy-L-arginine
2-amino-5,6-dihydro-4h-1,3-thiazine
2-amino-5,6-dihydro-4H-1,3-thiazine: RN given refers to parent cpd		1.9910
dactinomycin
Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)		210actinomycinmutagen
oxazolone
Oxazolone: Immunologic adjuvant and sensitizing agent.		2.0410
n(6)-(1-iminoethyl)lysine
N(6)-acetimidoyl-L-lysine : An L-lysine derivative that is L-lysine in which one of the hydrogens attached to N(6) is substituted by an acetimidoyl group		1.9910L-lysine derivative;
non-proteinogenic L-alpha-amino acid
ConditionIndicatedRelationship StrengthStudiesTrials
Contact Dermatitis
[description not available]		01.9910
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		01.9910