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Compound Detail

CHEMBL256147

TILARGININE
🧪 Phase III
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🧪 Phase III
CNC(=N)NCCC[C@H](N)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL256147
Name TILARGININE
Phase Phase III
Structure Type MOL
InChI Key NTNWOCRCBQPEKQ-YFKPBYRVSA-N

Known Names

.omega.-n-methylarginine L-NMMA Ng-methylarginine Ng-monomethyl-l-arginine Omega-n-methylarginine Omega-n-methylated arginine Tilarginina Tilarginine
20
Targets
145
Activities
3
Assay Types
0
PK Parameters
20
Publications
8
Known Names
11
Indications
1
Mechanisms

Molecular Properties

188.2
MW (Da)
-1.08
ALogP
3
HBA
5
HBD
111.2
PSA (Ų)
0.21
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Year 2000

Extended Properties

Molecular Formula C7H16N4O2
MW 188.23
Aromatic Rings 0
Heavy Atoms 13
NP-Likeness 1.41

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Nitric oxide synthase inhibitor INHIBITOR Nitric oxide synthase ✓ ✓

Indications

Anemia Anemia, Sickle Cell Hyperlipidemias Breast Neoplasms Endotoxemia Heart Failure HIV Infections Hypertension Hypoxia Liver Cirrhosis Sarcopenia

Activity Summary

IC50 128 meas. best 8.74
Ki 16 meas. best 6.7
EC50 1 meas. best 4.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nitric oxide synthase, inducible
CHEMBL4481
 IC50 8.74 5.875 1.8 12
Nitric oxide synthase 1
CHEMBL3568
 IC50 7.05 5.8838 90.0 8
Nitric oxide synthase 1
CHEMBL3048
 IC50 7.0 6.03 100.0 4
Nitric oxide synthase 1
CHEMBL3048
 Ki 6.7 6.0 200.0 3
Unchecked
CHEMBL612545
 Ki 6.62 5.85 240.0 4
Nitric oxide synthase 3
CHEMBL4803
 IC50 6.52 5.9464 300.0 11
Nitric oxide synthase 3
CHEMBL4803
 Ki 6.4 6.4 400.0 2
Nitric oxide synthase 1
CHEMBL3568
 Ki 6.08 6.08 840.0 2
Nitric oxide synthase, inducible
CHEMBL4481
 Ki 6.07 6.07 860.0 2
Nitric oxide synthase, inducible
CHEMBL3464
 IC50 5.64 4.8625 2300.0 8
RAW264.7
CHEMBL612557
 IC50 5.57 4.5816 2690.0 25
Mus musculus
CHEMBL375
 IC50 5.56 4.8025 2730.0 4
Rattus norvegicus
CHEMBL376
 IC50 5.52 5.52 3000.0 1
Nitric oxide synthase 1
CHEMBL4719
 IC50 5.37 5.37 4300.0 1
Nitric oxide synthase 3
CHEMBL4802
 Ki 5.23 5.23 5900.0 1
Nitric oxide synthase 3
CHEMBL4802
 IC50 5.16 5.16 7000.0 1
BV-2
CHEMBL614781
 IC50 5.0 4.7232 10000.0 31
Rattus norvegicus
CHEMBL376
 EC50 4.85 4.85 14000.0 1
Nitric oxide synthase, inducible
CHEMBL3464
 Ki 4.85 4.85 14000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.84 4.7114 14400.0 7
Nitric oxide synthase, inducible
CHEMBL3051
 IC50 4.75 4.75 18000.0 1
Unchecked
CHEMBL612545
 IC50 4.72 4.48 19200.0 2
DLD-1
CHEMBL614285
 IC50 4.68 4.68 21000.0 1
J774.1
CHEMBL4296442
 IC50 4.58 4.525 26000.0 4
J774
CHEMBL614123
 IC50 4.58 4.58 26000.0 1
ADMET
CHEMBL612558
 IC50 4.57 4.57 27100.0 1
Macrophage
CHEMBL612578
 IC50 4.55 4.395 28000.0 2
Prostaglandin E synthase
CHEMBL5658
 Ki 4.53 4.53 29670.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nitric oxide synthase, inducible IC50 = 1.8 nM 8.74 Inhibition of human recombinant iNOS assessed as conversion of [3H]L-arginine to... 24900459
Nitric oxide synthase 1 IC50 = 90.0 nM 7.05 Inhibitory activity against human neuronal nitric oxide synthase 12620067
Nitric oxide synthase 1 IC50 = 100.0 nM 7.0 Ability to inhibit the conversion of [3H]-L-Arg to [3H]L-citrulline catalyzed by... 11327581
Nitric oxide synthase 1 IC50 = 100.0 nM 7.0 Inhibition of conversion of [3H]L-Arg to [3H]L-citrulline catalyzed by neuronal ... 11327580
Nitric oxide synthase 1 Ki = 200.0 nM 6.7 Inhibition of rat nNOS 23458846
Unchecked Ki = 240.0 nM 6.62 Inhibition of COX-2 (unknown origin) 38522589
Nitric oxide synthase 3 IC50 = 300.0 nM 6.52 Ability to inhibit the conversion of [3H]L-Arg to [3H]L-citrulline catalyzed by ... 11327581
Nitric oxide synthase, inducible IC50 = 300.0 nM 6.52 Ability to inhibit the conversion of [3H]L-Arg to [3H]L-citrulline catalyzed by ... 11327581
Nitric oxide synthase, inducible IC50 = 300.0 nM 6.52 Ability to inhibit conversion of [3H]L-Arg to [3H]L-citrulline catalyzed by indu... 11327580
Nitric oxide synthase 3 IC50 = 300.0 nM 6.52 Ability to inhibit conversion of [3H]L-Arg to [3H]L-citrulline catalyzed by endo... 11327580
Nitric oxide synthase 3 IC50 = 330.0 nM 6.48 Inhibitory activity against human endothelial nitric oxide synthase 12620067
Nitric oxide synthase, inducible IC50 = 340.0 nM 6.47 Inhibitory activity of compound against human inducible nitric oxide synthase 12620067
Nitric oxide synthase 3 Ki = 400.0 nM 6.4 Inhibitory activity against human endothelial nitric oxide synthase (eNOS) isoen... 9667974
Nitric oxide synthase 3 Ki = 400.0 nM 6.4 Inhibitory constant for the inhibition of human Endothelial nitric oxide synthas... -
Nitric oxide synthase 1 Ki = 500.0 nM 6.3 Inhibition of rat nNOS transfected in HEK293 cells assessed as inhibition consta... 36063653
Nitric oxide synthase 3 IC50 = 540.0 nM 6.27 Inhibitory concentration against recombinant human Endothelial nitric oxide synt... 12781178
Nitric oxide synthase 3 IC50 = 540.0 nM 6.27 In vitro inhibition of endothelial nitric oxide synthase. 12182860
Nitric oxide synthase 3 IC50 = 650.0 nM 6.19 Inhibition of human eNOS expressed in Sf9 cells assessed as reduction in convers... 22335555
Nitric oxide synthase 3 IC50 = 650.0 nM 6.19 Inhibition of human recombinant eNOS assessed as conversion of [3H]L-arginine to... 24900459
Nitric oxide synthase 1 Ki = 840.0 nM 6.08 Inhibitory constant for the inhibition of human Neuronal nitric oxide synthase -

Literature References

PubMed DOI Target Context # Activities
17895252 10.1074/jbc.m707231200 N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 9
38522589 10.1016/j.bmcl.2024.129714 RAW264.7 7
15270564 10.1021/np030529k Macrophage 6
10560729 10.1016/s0960-894x(99)00536-3 Mus musculus 6
26898337 10.1016/j.bmcl.2016.02.023 RAW264.7 5
12398545 10.1021/np020078o Macrophage 5
11514174 10.1016/s0960-894x(01)00413-9 Mus musculus 5
12762798 10.1021/np0205710 Macrophage 5
15270564 10.1021/np030529k ADMET 5
27777005 10.1016/j.bmcl.2016.10.034 Mus musculus 5
38959374 10.1021/acs.jmedchem.4c00950 RAW264.7 3
17895252 10.1074/jbc.m707231200 Unchecked 3
29685654 10.1016/j.bmcl.2018.04.037 RAW264.7 3
9651169 10.1021/jm980073h Rattus norvegicus 3
16643064 10.1021/np0600346 RAW264.7 3
10543912 10.1021/np990116c RAW264.7 3
38522589 10.1016/j.bmcl.2024.129714 Unchecked 3
20738102 10.1021/np100233d HL-60 2
19013076 10.1016/j.bmc.2008.10.058 N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 2
19900811 10.1016/j.bmcl.2009.10.016 BV-2 2

Data from ChEMBL 36 via Core Engine