Page last updated: 2024-08-05 14:59:28

EC 1.14.13.39 (nitric oxide synthase) inhibitor

An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).

ChEBI ID: 61908

Members (21)

MemberDefinitionClass
5,7-dihydroxy-6-methoxy-2-phenylchromen-4-oneA dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-6.oroxylin A
ainsliadimer aA sesquiterpene lactone isolated from the whole plants of Ainsliaea macrocephala; exhibits inhibitory activity against production of nitric oxide (NO).ainsliadimer A
bis(7)-tacrineA secondary amino compound consisting of two molecules of tacrine that are linked together through their exocyclic amino groups by a heptane-1,7-diyl chain. Bis(7)-tacrine is an acetylcholinesterase (AChE)inhibitor (IC50 0.40 nM, >1,000 times more potent than tacrine). It has also been found to protect against H2O2 -induced apoptosis in rat pheochromocytoma cells.bis(7)-tacrine
citrullineThe L-enantiomer of citrulline.L-citrulline zwitterion; L-citrulline
dihydroxanthohumolA member of the class of dihydrochalcones that is the alpha,beta-dihydro derivative of xanthohumol. Isolated from Humulus lupulus, it exhibits inhibition of NO production.dihydroxanthohumol
formamidineThe smallest member of the class of carboxamidines being formic acid with the O and OH groups from the carboxy function replaced by NH and NH2 groups respectively. The parent of the class of formamidines.formamidine
glutamineAn optically active form of glutamine having L-configuration.L-glutamine zwitterion; L-glutamine
methylguanidineA guanidine in which one of the amino hydrogens of guanidine itself is substituted by a methyl group.methylguanidine
myricitrinA glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity.myricitrin
n-(3-(aminomethyl)benzyl)acetamidineAn aralkylamine that is Nbenzylacetamidine substituted at position 3 on the benzene ring by an aminomethyl group. An inhibitor of nitric oxide synthase.N-[3-(aminomethyl)benzyl]acetamidine
n,n-dimethylarginineA L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group.N(omega),N(omega)-dimethyl-L-arginine
ng-nitroarginine methyl esterAn alpha-amino acid ester that is the methyl ester of N(gamma)-nitro-L-arginine.N(gamma)-nitro-L-arginine methyl ester
ng-nitroarginine methyl esterA hydrochloride obtained by combining N(gamma)-nitro-L-arginine methyl ester with one equivalent of hydrochloric acid.N(gamma)-nitro-L-arginine methyl ester hydrochloride
nitroflurbiprofenA carboxylic ester obtained by formal condensation of the carboxy group of flurbiprofen with the free hydroxy group of 4-(nitrooxy)butanol. It is a non-steroidal anti-inflammatory agent showing inhibitory effects against the cyclooxygenases COX1 and COX2.nitroflurbiprofen
p-hydroxycinnamaldehydeA cinnamaldehyde that is (E)-cinnamaldehyde substituted at position 4 on the phenyl ring by a hydroxy group.4-hydroxycinnamaldehyde
pimagedineA one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.aminoguanidine
propylthiouracilA pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.6-propyl-2-thiouracil
s-methylthiocitrullineAn L-arginine derivative in which the guanidino NH2 group of L-arginine is replaced by a methylsufanyl group.S-methyl-L-thiocitrulline
symmetric dimethylarginineA L-arginine derivative having two methyl groups at the N(omega)- and N'(omega)-positionsN(omega),N'(omega)-dimethyl-L-arginine zwitterion; N(omega),N'(omega)-dimethyl-L-arginine
yakuchinone-aA ketone that is heptan-3-one substituted by a 4-hydroxy-3-methoxyphenyl group at position 1 and a phenyl group at position 7. Isolated from in Alpinia oxyphylla, it exhibits antineoplastic and inhibitory activities against COX-1, COX-2 and NO synthase.1-(4'-hydroxy-3'-methoxyphenyl)-7-phenyl-3-heptanone
zaluzanin CA sesquiterpene lactone that is decahydroazuleno[4,5-b]furan-2(3H)-one substituted by methylidene groups at positions 3, 6 and 9 and a hydroxy group at position 8.zaluzanin C

Research

Studies (43,481)

TimeframeStudies, Drugs with This Role(%)All Drugs %
pre-19908,426 (19.38)18.7374
1990's9,532 (21.92)18.2507
2000's12,619 (29.02)29.6817
2010's9,989 (22.97)24.3611
2020's2,915 (6.70)2.80

Study Types

Publication TypeStudies, Drugs with this Role (%)All Drugs (%)
Trials1,503 (3.22%)5.53%
Reviews2,725 (5.83%)6.00%
Case Studies1,137 (2.43%)4.05%
Observational89 (0.19%)0.25%
Other41,290 (88.33%)84.16%

Protein Targets (167)

Potency Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)Drugs
15-lipoxygenase, partialHomo sapiens (human)Potency39.810711
2,3-bisphosphoglycerate-independent phosphoglycerate mutaseLeishmania major strain FriedlinPotency0.016911
67.9K proteinVaccinia virusPotency18.867722
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency24.445113
arylsulfatase AHomo sapiens (human)Potency6.749514
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency17.816222
Bloom syndrome protein isoform 1Homo sapiens (human)Potency0.002822
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency50.118711
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency15.211312
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency28.183811
Chain A, Beta-lactamaseEscherichia coli K-12Potency44.668412
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency55.527812
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency13.614014
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency12.850713
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.891311
chromobox protein homolog 1Homo sapiens (human)Potency47.568723
cytochrome P450 2C19 precursorHomo sapiens (human)Potency6.581212
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.924424
DNA polymerase betaHomo sapiens (human)Potency10.000011
DNA polymerase eta isoform 1Homo sapiens (human)Potency39.810711
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency71.478923
DNA polymerase kappa isoform 1Homo sapiens (human)Potency18.912413
estrogen nuclear receptor alphaHomo sapiens (human)Potency24.042024
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency19.831218
EWS/FLI fusion proteinHomo sapiens (human)Potency23.469833
flap endonuclease 1Homo sapiens (human)Potency4.130126
GABA theta subunitRattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.924412
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.924412
gemininHomo sapiens (human)Potency2.645926
glp-1 receptor, partialHomo sapiens (human)Potency2.511911
GLS proteinHomo sapiens (human)Potency10.736222
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency1.995311
histone-lysine N-methyltransferase 2A isoform 2 precursorHomo sapiens (human)Potency14.125411
hypothetical protein, conservedTrypanosoma bruceiPotency50.118711
IDH1Homo sapiens (human)Potency29.092911
interleukin 8Homo sapiens (human)Potency74.978011
lamin isoform A-delta10Homo sapiens (human)Potency0.000911
lethal factor (plasmid)Bacillus anthracis str. A2012Potency26.364813
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency3.162311
Microtubule-associated protein tauHomo sapiens (human)Potency11.676925
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency2.511911
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency12.589311
NFKB1 protein, partialHomo sapiens (human)Potency9.501226
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency4.466811
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency42.163211
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency25.929011
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency35.481311
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency44.964712
peripheral myelin protein 22 isoform 1Homo sapiens (human)Potency84.921411
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency44.668411
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency63.626111
phosphopantetheinyl transferaseBacillus subtilisPotency47.023614
pregnane X nuclear receptorHomo sapiens (human)Potency70.757611
Rap guanine nucleotide exchange factor 3Homo sapiens (human)Potency89.125111
regulator of G-protein signaling 4Homo sapiens (human)Potency0.075211
serine-protein kinase ATM isoform aHomo sapiens (human)Potency22.387211
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency37.685811
Smad3Homo sapiens (human)Potency22.387211
TDP1 proteinHomo sapiens (human)Potency20.766028
thioredoxin reductaseRattus norvegicus (Norway rat)Potency1.228315
thyroid stimulating hormone receptorHomo sapiens (human)Potency5.987426
USP1 protein, partialHomo sapiens (human)Potency12.589311
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency0.001611

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)Drugs
AcetylcholinesteraseElectrophorus electricus (electric eel)IC500.000733
AcetylcholinesteraseHomo sapiens (human)IC500.001188
AcetylcholinesteraseMus musculus (house mouse)IC500.001911
AcetylcholinesteraseRattus norvegicus (Norway rat)IC500.01581214
AcetylcholinesteraseHomo sapiens (human)Ki0.001624
Acetylcholinesterase Bos taurus (cattle)Ki0.001344
Aldo-keto reductase family 1 member B1Rattus norvegicus (Norway rat)IC5030.000011
Amino acid transporterRattus norvegicus (Norway rat)IC501,831.780055
Amyloid-beta precursor proteinHomo sapiens (human)IC508.400011
AromataseHomo sapiens (human)IC502.900013
Asc-type amino acid transporter 1Rattus norvegicus (Norway rat)IC5041.000011
ATP-binding cassette sub-family C member 3Homo sapiens (human)IC50133.000011
Aurora kinase BHomo sapiens (human)IC503.890011
Beta-secretase 1Homo sapiens (human)IC507.500033
Bile salt export pumpHomo sapiens (human)IC50133.000011
calpain II, partialSus scrofa (pig)IC505.000411
Canalicular multispecific organic anion transporter 1Homo sapiens (human)IC50133.000011
Carboxylic ester hydrolase Equus caballus (horse)IC500.010011
Carboxylic ester hydrolase Rattus norvegicus (Norway rat)IC500.167555
Carboxylic ester hydrolase Equus caballus (horse)Ki0.002033
caspase-3 isoform a preproproteinHomo sapiens (human)IC50100.000011
CholinesteraseEquus caballus (horse)IC500.005133
CholinesteraseHomo sapiens (human)IC500.014245
CholinesteraseMus musculus (house mouse)IC500.009111
CholinesteraseEquus caballus (horse)Ki0.002011
CholinesteraseHomo sapiens (human)Ki0.000211
Collagenase 3Homo sapiens (human)IC5037.350012
Complement C1s subcomponentHomo sapiens (human)Ki18,100.000011
Cytochrome P450 2C19Homo sapiens (human)IC500.005311
Cytochrome P450 3A4Homo sapiens (human)IC500.005312
Gamma-aminobutyric acid receptor subunit alpha-1Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit alpha-2Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit alpha-3Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit alpha-4Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit alpha-5Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit alpha-6Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit beta-1Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit beta-2Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit beta-3Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit deltaHomo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit epsilonHomo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit gamma-1Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit gamma-2Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit gamma-3Homo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit piHomo sapiens (human)IC506.000011
Gamma-aminobutyric acid receptor subunit thetaHomo sapiens (human)IC506.000011
integrase, partialHuman immunodeficiency virus 1IC504.944022
lens epithelium-derived growth factor p75Homo sapiens (human)IC504.944022
MPI proteinHomo sapiens (human)IC5030.965011
Multidrug resistance-associated protein 4Homo sapiens (human)IC50133.000011
MyeloperoxidaseHomo sapiens (human)IC502.810011
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)Ki1,175.187514
NADH-cytochrome b5 reductase 3 Homo sapiens (human)IC50279.400011
Neutral amino acid transporter AHomo sapiens (human)IC503,373.000011
Neutral amino acid transporter B(0)Homo sapiens (human)IC50541.000011
Neutrophil elastaseHomo sapiens (human)IC5037.350012
Nitric oxide synthase, brainHomo sapiens (human)IC5015.308989
Nitric oxide synthase, brainHomo sapiens (human)Ki785.225036
Nitric oxide synthase, brain Rattus norvegicus (Norway rat)IC505.053333
Nitric oxide synthase, brain Rattus norvegicus (Norway rat)Ki1,175.187514
Nitric oxide synthase, endothelialBos taurus (cattle)IC50483.500044
Nitric oxide synthase, endothelialHomo sapiens (human)IC50178.05671012
Nitric oxide synthase, endothelial Rattus norvegicus (Norway rat)IC502.900011
Nitric oxide synthase, inducibleHomo sapiens (human)IC50100,011.06771114
Nitric oxide synthase, inducibleMus musculus (house mouse)IC5013.677999
Nitric oxide synthase, inducibleRattus norvegicus (Norway rat)IC50132.010011
Polyphenol oxidase 2Agaricus bisporusIC50220.000022
Receptor-type tyrosine-protein kinase FLT3Homo sapiens (human)IC501.480011
RNA-editing ligase 1, mitochondrialTrypanosoma brucei bruceiIC5051.381011
sentrin-specific protease 8Homo sapiens (human)IC5013.300011
SUMO-1-specific proteaseHomo sapiens (human)IC5010.000011
SUMO1/sentrin specific peptidase 7Homo sapiens (human)IC507.820011
Thyroid peroxidaseHomo sapiens (human)IC503.380011
Trypsin-1Homo sapiens (human)IC5061.000011
Trypsin-2Homo sapiens (human)IC5061.000011
Trypsin-3Homo sapiens (human)IC5061.000011

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)Drugs
AlbuminBos taurus (cattle)EC5026,000.000011
Chain A, Glutamine Binding ProteinEscherichia coliKd0.500011
delta-type opioid receptorHomo sapiens (human)EC5064.584011
glycogen synthase kinase-3 beta isoform 1Homo sapiens (human)EC50300.000012
melanocortin receptor 4Homo sapiens (human)EC5089.202012
mu-type opioid receptor isoform MOR-1Homo sapiens (human)EC5064.584011
POsterior SegregationCaenorhabditis elegansEC5015.805011
Sodium-dependent noradrenaline transporter Homo sapiens (human)EC5014.047011
streptokinase A precursorStreptococcus pyogenes M1 GASEC502.757011
Taste receptor type 2 member 38Homo sapiens (human)EC502.000011
Zinc finger protein mex-5Caenorhabditis elegansEC5014.047011

Other Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)Drugs
Carbonic anhydrase 1Homo sapiens (human)KA100.000011
Carbonic anhydrase 2Homo sapiens (human)KA50.000011
Carbonic anhydrase-like protein, putativeTrypanosoma cruzi strain CL BrenerKA2.850011
Cyclic AMP-responsive element-binding protein 1Homo sapiens (human)AC502.200011
General amino-acid permease GAP1Saccharomyces cerevisiae S288CKm37.000011
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Bos taurus (cattle)Km810.000011
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Homo sapiens (human)Km178.333323
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1Rattus norvegicus (Norway rat)Km180.000011
Prolyl 4-hydroxylase, beta polypeptideHomo sapiens (human)AC509.800022
Receptor-type tyrosine-protein phosphatase betaHomo sapiens (human)Kis125.700011
Taste receptor type 2 member 38Homo sapiens (human)Activity0.300011