Page last updated: 2024-11-08

vinyl-l-nio

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

Cross-References

ID SourceID
PubMed CID447181
SCHEMBL ID2184864
MeSH IDM0289502

Synonyms (11)

Synonym
(2s)-2-amino-5-(1-aminobut-3-enylideneamino)pentanoic acid
AKOS006278503
gtpl8830
l-vnio
compound 2e [pmid: 19013076]
n5 -(1-imino-3-butenyl)-l-ornithine
SCHEMBL2184864
vinyl-l-nio
hddah inhibitor, 1a
bdbm235685
Q27076518
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)IC50 (µMol)13.00007.80008.25708.7140AID412445
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)Ki2.00000.05001.49292.0000AID1581785; AID1803038; AID412445
Nitric oxide synthase, brainHomo sapiens (human)Ki0.10000.01501.18117.3000AID404423
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

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

Molecular Functions (19)

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

Ceullar Components (18)

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

Bioassays (19)

Assay IDTitleYearJournalArticle
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.
AID1581787Inhibition of neuronal NOS (unknown origin) assessed as formation of methemoglobin from oxyhemoglobin at 1 mM using L-arginine as substrate in presence of oxyhemoglobin and NADPH by UV-vis spectrophotometry relative to control2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Discovery of
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.
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.
AID1581786Inhibition of bovine liver arginase at 1 mM using L-arginine as substrate measured after 30 mins by colder reagent based microplate reader assay relative to control2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Discovery of
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.
AID1581788Inhibition of endothelial NOS (unknown origin) assessed as formation of methemoglobin from oxyhemoglobin at 1 mM using L-arginine as substrate in presence of oxyhemoglobin and NADPH by UV-vis spectrophotometry relative to control2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Discovery of
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.
AID404423Inhibition of nNOS assessed as conversion of L-[3H]arginine to L-[3H]citrulline2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
Design, synthesis, and evaluation of potential inhibitors of nitric oxide synthase.
AID1581785Inhibition of 6xHis-tagged recombinant human DDAH1 expressed in Escherichia coli BL21 cells using NMMA as substrate measured after 30 mins by colder reagent based microplate reader assay2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Discovery of
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.
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.
AID412455Inhibition of human recombinant NOS2008Bioorganic & 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.
AID1581789Inhibition of iNOS (unknown origin) assessed as formation of methemoglobin from oxyhemoglobin at 1 mM using L-arginine as substrate in presence of oxyhemoglobin and NADPH by UV-vis spectrophotometry relative to control2020Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1
Discovery of
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.
AID1345168Human NG,NG-Dimethylarginine dimethylaminohydrolase 1 (Dimethylarginine dimethylaminohydrolases)2008Bioorganic & 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.
[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's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's1 (20.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.87

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 Index12.87 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.87)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]