Compounds > omega-n-allylarginine
Page last updated: 2024-10-15

omega-n-allylarginine

Description

omega-N-allylarginine: inhibitor of nitric oxide synthase; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135409360
CHEMBL ID106425
SCHEMBL ID21067907
MeSH IDM0199309

Synonyms (21)

Synonym
ARV ,
bdbm50240714
n-omega-allyl-l-arginine
(2s)-5-{[(allylamino)(iminio)methyl]amino}-2-ammoniopentanoate
(s)-5-(n''-allyl-guanidino)-2-amino-pentanoic acid
CHEMBL106425 ,
omega-n-allylarginine
l-ornithine, n5-(imino(2-propenylamino)methyl)-
139461-37-3
n(g)-allylarginine
DTXSID50161054
bdbm235689
hddah inhibitor, 2c
SCHEMBL21067907
HY-115750
n|o-allyl-l-arginine
(2s)-2-amino-5-[[amino-(prop-2-enylamino)methylidene]amino]pentanoic acid
(2s)-2-amino-5-({amino[(prop-2-en-1-yl)amino]methylidene}amino)pentanoic acid
CS-0255245
n??-allyl-l-arginine
AKOS040756726
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)IC50 (µMol)207.00007.80008.25708.7140AID412445
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)Ki58.00000.05001.49292.0000AID1803038; AID412445
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
cytosolN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
extracellular exosomeN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID412451Inhibition of human recombinant nNOS at 1 uM2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID412448Inhibition of human recombinant nNOS at 100 uM2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID67988Selectivity index which is the ratio of the Ki or IC50 values of recombinant bovine Endothelial nitric oxide synthase and bovine brain nNOS (Neuronal nitric oxide synthase)1999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
N(omega)-Nitroarginine-containing dipeptide amides. Potent and highly selective inhibitors of neuronal nitric oxide synthase.
AID412445Inhibition of human DDAH1 by plate-reader assay2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID67989Selectivity index which is the ratio of the Ki or IC50 values of recombinant bovine eNOS (Endothelial nitric oxide synthase) / recombinant murine iNOS (Inducible nitric oxide synthase)1999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
N(omega)-Nitroarginine-containing dipeptide amides. Potent and highly selective inhibitors of neuronal nitric oxide synthase.
AID412452Inhibition of human recombinant eNOS at 1 uM2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID412450Inhibition of human recombinant iNOS at 1 uM2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID412449Inhibition of human recombinant eNOS at 100 uM2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID412453Inhibition of human recombinant iNOS at 100 uM2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID412444Inhibition of human DDAH1 at 1 mM by HPLC2008Bioorganic & medicinal chemistry, Dec-15, Volume: 16, Issue:24
Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.
AID147240Compound was tested for the inhibition of inducible murine macrophage nitric oxide(NO) synthase1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
NG-allyl- and NG-cyclopropyl-L-arginine: two novel inhibitors of macrophage nitric oxide synthase.
AID147239Compound was tested for the inhibition of inducible murine macrophage nitric oxide(NO) synthase, activity expressed as inhibitory constant1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
NG-allyl- and NG-cyclopropyl-L-arginine: two novel inhibitors of macrophage nitric oxide synthase.
AID147241Compound was tested for the inhibition of inducible murine macrophage expressed as inactivation constant1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
NG-allyl- and NG-cyclopropyl-L-arginine: two novel inhibitors of macrophage nitric oxide synthase.
AID1803038In Vitro hDDAH-1 Assay from Article 10.3109/14756366.2011.573480: \\Designing modulators of dimethylarginine dimethylaminohydrolase (DDAH): a focus on selectivity over arginase.\\2012Journal of enzyme inhibition and medicinal chemistry, Feb, Volume: 27, Issue:1
Designing modulators of dimethylarginine dimethylaminohydrolase (DDAH): a focus on selectivity over arginase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (40.00)18.2507
2000's2 (40.00)29.6817
2010's1 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
n-(3-(aminomethyl)benzyl)acetamidine
N-(3-(aminomethyl)benzyl)acetamidine: structure in first source. N-[3-(aminomethyl)benzyl]acetamidine : An aralkylamine that is Nbenzylacetamidine substituted at position 3 on the benzene ring by an aminomethyl group. An inhibitor of nitric oxide synthase.		210aralkylamine;
carboxamidine;
primary amino compound		angiogenesis inhibitor;
EC 1.14.13.39 (nitric oxide synthase) inhibitor;
geroprotector
2-amino-5,6-dihydro-6-methyl-4h-1,3-thiazine
2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine: a selective inhibitor of nitric oxide synthase; structure given in first source		2101,3-thiazine
7-nitroindazole
7-nitroindazole: an inhibitor of nitric oxide synthase; exhibits anti-nociceptive activity without increasing blood pressure		210
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.		210guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor
s-ethyl n-(4-(trifluoromethyl)phenyl)isothiourea
S-ethyl N-(4-(trifluoromethyl)phenyl)isothiourea: structure in first source		210
etiron
etiron: a nitric oxide synthase inhibitor; RN given refers to parent cpd; structure		210
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.		2.3920arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical
acrolein
[no description available]		210enalherbicide;
human xenobiotic metabolite;
toxin
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		210dihydrogen
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.		210imidothiocarbamic 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]		2.7230L-alpha-amino acid
omega-n-methylarginine
omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.		2.6930amino acid zwitterion;
arginine derivative;
guanidines;
L-arginine derivative;
non-proteinogenic L-alpha-amino acid
nitroarginine
Nitroarginine: An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6). N(gamma)-nitro-L-arginine : An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.		2.7230guanidines;
L-arginine derivative;
N-nitro compound;
non-proteinogenic L-alpha-amino acid
vinyl-l-nio
[no description available]		2.7230
ConditionIndicatedRelationship StrengthStudiesTrials