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Compound Detail

CHEMBL277498

NIPECOTIC ACID
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O=C(O)C1CCCNC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL277498
Name NIPECOTIC ACID
Phase Preclinical
Structure Type MOL
InChI Key XJLSEXAGTJCILF-UHFFFAOYSA-N
9
Targets
36
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

129.2
MW (Da)
0.07
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.53
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C6H11NO2
MW 129.16
Aromatic Rings 0
Heavy Atoms 9
NP-Likeness 0.17

Activity Summary

IC50 34 meas. best 8.0
Ki 2 meas. best 5.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium- and chloride-dependent GABA transporter 1
CHEMBL1903
 IC50 8.0 6.0667 10.1 3
Rattus norvegicus
CHEMBL376
 Ki 5.42 5.42 3800.0 1
Rattus norvegicus
CHEMBL376
 IC50 5.41 5.215 3940.0 4
Unchecked
CHEMBL612545
 IC50 5.32 5.0025 4770.0 4
GABA transporter
CHEMBL2111478
 IC50 5.22 5.22 6000.0 1
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 IC50 5.1 4.985 7943.3 6
GABA transporter 4
CHEMBL3699
 IC50 4.71 4.69 19498.5 5
GABA transporter 3
CHEMBL5205
 IC50 4.64 4.64 22908.7 2
Sodium- and chloride-dependent GABA transporter 2
CHEMBL4889
 IC50 4.41 4.41 39000.0 1
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 Ki 4.24 4.24 58210.3 1
Sodium- and chloride-dependent GABA transporter 2
CHEMBL4535
 IC50 4.18 4.18 66000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium- and chloride-dependent GABA transporter 1 IC50 = 10.1 nM 8.0 Percent inhibition against GABA transporter at a compound concentration of 1 uM 16250647
Rattus norvegicus Ki = 3800.0 nM 5.42 Inhibition was measured for [3H]GABA-uptake from rat synaptosomal membrane. 3941406
Rattus norvegicus IC50 = 3940.0 nM 5.41 Inhibition of GABA uptake from rat diencephalon-midbrain, 2985785
Rattus norvegicus IC50 = 4000.0 nM 5.4 Inhibition of [3H]GABA (gamma amino butyric acid) uptake in vitro in rat brain s... 10206541
Unchecked IC50 = 4770.0 nM 5.32 Inhibition of GAT1-mediated [3H]GABA uptake in bovine brain stem 20219271
Rattus norvegicus IC50 = 5600.0 nM 5.25 The inhibitory concentration of compound against sodium dependent [3H]GABA synap... 2995665
GABA transporter IC50 = 6000.0 nM 5.22 Inhibition of high affinity neuronal GABA uptake by synaptosomes of rat brain me... 6292417
Unchecked IC50 = 7170.0 nM 5.14 Inhibition of rat GABA transporter 20875743
Sodium- and chloride-dependent GABA transporter 1 IC50 = 8000.0 nM 5.1 Inhibitory activity against human GABA transporter-1 (hGAT1) 8057281
Sodium- and chloride-dependent GABA transporter 1 IC50 = 7943.28 nM 5.1 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK293 cells after 25 m... 23336362
Sodium- and chloride-dependent GABA transporter 1 IC50 = 8000.0 nM 5.1 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK293 cells after 25 m... 23336362
Sodium- and chloride-dependent GABA transporter 1 IC50 = 8000.0 nM 5.1 Inhibition of human GAT1 expressed in COS cells assessed as decrease in [3H]GABA... 30777661
Sodium- and chloride-dependent GABA transporter 1 IC50 = 8511.38 nM 5.07 Inhibition of mouse GAT1 expressed in HEK cells assessed as inhibition of [3H]-G... 23598250
Sodium- and chloride-dependent GABA transporter 1 IC50 = 13304.54 nM 4.88 Inhibition of mouse GAT1 expressed in HEK293 cells assessed as [3H]GABA uptake p... 27039250
Sodium- and chloride-dependent GABA transporter 1 IC50 = 13182.57 nM 4.88 Inhibition of GABA uptake at murine GAT-1 expressed in HEK293 cells 23770450
Sodium- and chloride-dependent GABA transporter 1 IC50 = 13182.57 nM 4.88 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK cells 18395300
Rattus norvegicus IC50 = 16000.0 nM 4.8 Inhibition of Norepinephrine uptake from rat diencephalon-midbrain 2985785
Unchecked IC50 = 16218.1 nM 4.79 Inhibition of mouse GAT4 expressed in HEK cells assessed as inhibition of [3H]-G... 23598250
Unchecked IC50 = 17300.0 nM 4.76 Inhibition of GAT3-mediated [3H]GABA uptake in bovine brain stem 20219271
GABA transporter 4 IC50 = 19498.45 nM 4.71 Inhibition of mouse GAT3 expressed in HEK cells assessed as inhibition of [3H]-G... 23598250

Literature References

PubMed DOI Target Context # Activities
18327252 10.1038/nchembio.78 Drosophila 4
10762036 10.1016/s0960-894x(00)00064-0 Mus musculus 4
20170117 10.1021/jm901654x ADMET 3
2985785 10.1021/jm50001a020 No relevant target 3
27039250 10.1016/j.bmc.2016.03.038 GABA transporter 4 2
20219271 10.1016/j.ejmech.2010.02.029 Unchecked 2
6292417 10.1021/jm00352a012 No relevant target 2
23336362 10.1021/jm301800j Sodium- and chloride-dependent GABA transporter 1 2
2985785 10.1021/jm50001a020 Rattus norvegicus 2
2985785 10.1021/jm50001a020 GABA-A receptor; anion channel 2
27039250 10.1016/j.bmc.2016.03.038 Sodium- and chloride-dependent GABA transporter 1 2
2985785 10.1021/jm50001a020 Glutamate decarboxylase 1 1
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent betaine transporter 1
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent GABA transporter 3 1
30777661 10.1016/j.bmc.2019.02.015 Sodium- and chloride-dependent GABA transporter 1 1
10206541 10.1016/s0960-894x(99)00083-9 Rattus norvegicus 1
2985785 10.1021/jm50001a020 4-aminobutyrate aminotransferase, mitochondrial 1
6292417 10.1021/jm00352a012 GABA transporter 1
6292417 10.1021/jm00352a012 GABA-A receptor; anion channel 1
6276545 10.1021/jm00344a004 4-aminobutyrate aminotransferase, mitochondrial 1

Data from ChEMBL 36 via Core Engine