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Compound Detail

CHEMBL77575

(R)-NIPECOTIC ACID
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O=C(O)[C@@H]1CCCNC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL77575
Name (R)-NIPECOTIC ACID
Phase Preclinical
Structure Type MOL
InChI Key XJLSEXAGTJCILF-RXMQYKEDSA-N
11
Targets
50
Activities
1
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 50 meas. best 5.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rattus norvegicus
CHEMBL376
 IC50 5.77 5.3625 1690.0 4
Sodium- and chloride-dependent GABA transporter 1
CHEMBL4054
 IC50 5.73 5.6379 1880.0 14
Unchecked
CHEMBL612545
 IC50 5.67 5.2 2150.0 2
GABA transporter 2
CHEMBL4228
 IC50 5.4 5.2 4000.0 2
Sodium- and chloride-dependent GABA transporter 1
CHEMBL1903
 IC50 5.23 4.9425 5900.0 4
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 IC50 5.19 4.9825 6456.5 4
Mus musculus
CHEMBL375
 IC50 4.92 4.86 12000.0 2
GABA transporter 4
CHEMBL3699
 IC50 4.79 4.5367 16218.1 3
Sodium- and chloride-dependent GABA transporter 2
CHEMBL4889
 IC50 4.72 4.72 19000.0 1
GABA transporter 3
CHEMBL5205
 IC50 4.71 4.71 19498.5 2
Sodium- and chloride-dependent GABA transporter 3
CHEMBL5208
 IC50 4.29 4.29 51000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rattus norvegicus IC50 = 1690.0 nM 5.77 Inhibition of GABA uptake from rat diencephalon-midbrain, 2985785
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1880.0 nM 5.73 H-bonding interaction between amino acid residue (Tyr-140) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1900.0 nM 5.72 H-bonding interaction between amino acid residue (Asn-137) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1950.0 nM 5.71 H-bonding interaction between amino acid residue (Asn-137) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1970.0 nM 5.71 H-bonding interaction between amino acid residue (Tyr-140) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1940.0 nM 5.71 H-bonding interaction between amino acid residue (Ser-133) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2000.0 nM 5.7 H-bonding interaction between amino acid residue (Ser-133) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2140.0 nM 5.67 H-bonding interaction between amino acid residue (Thr-89) of Sodium- and chlorid... 15509161
Unchecked IC50 = 2150.0 nM 5.67 Inhibition of GAT1-mediated [3H]GABA uptake in bovine brain stem 20219271
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2560.0 nM 5.59 H-bonding interaction between amino acid residue (Thr-89) of Sodium- and chlorid... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2600.0 nM 5.58 H-bonding interaction between amino acid residue (Asn-137) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2630.0 nM 5.58 H-bonding interaction between amino acid residue (Tyr-140) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2690.0 nM 5.57 H-bonding interaction between amino acid residue (Asn-137) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2740.0 nM 5.56 H-bonding interaction between amino acid residue (Ser-133) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2780.0 nM 5.56 H-bonding interaction between amino acid residue (Tyr-140) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2860.0 nM 5.54 H-bonding interaction between amino acid residue (Ser-133) of Sodium- and chlori... 15509161
GABA transporter 2 IC50 = 4000.0 nM 5.4 Inhibition of [3H]GABA uptake at GAT2 in mouse neurons after 3 mins by scintilla... 23398473
Rattus norvegicus IC50 = 5000.0 nM 5.3 Inhibition of GABA uptake into crude synaptosomes prepared from adult rat brain 10639282
Rattus norvegicus IC50 = 5200.0 nM 5.28 In vitro inhibition of [3H]GABA uptake in rat Hippocampal slices. 1433224
Sodium- and chloride-dependent GABA transporter 1 IC50 = 5900.0 nM 5.23 Inhibition of human GAT1 transfected in CHO cells assessed as [3H]GABA uptake af... 23886812

Literature References

PubMed DOI Target Context # Activities
15509161 10.1021/jm040809c Sodium- and chloride-dependent GABA transporter 1 14
23398473 10.1021/jm301872x GABA transporter 2 5
1433224 10.1021/jm00100a032 Rattus norvegicus 2
10639282 10.1021/jm9904452 Mus musculus 2
23398473 10.1021/jm301872x Sodium- and chloride-dependent GABA transporter 1 2
23398473 10.1021/jm301872x GABA transporter 3 2
23398473 10.1021/jm301872x GABA transporter 4 2
20219271 10.1016/j.ejmech.2010.02.029 Unchecked 2
30777661 10.1016/j.bmc.2019.02.015 Sodium- and chloride-dependent GABA transporter 1 1
2985785 10.1021/jm50001a020 Rattus norvegicus 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 4 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 3 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 2 1
18395300 10.1016/j.ejmech.2008.01.005 Sodium- and chloride-dependent GABA transporter 1 1
17517506 10.1016/j.bmcl.2007.04.010 Sodium- and chloride-dependent GABA transporter 1 1
16246548 10.1016/j.bmcl.2005.09.004 Sodium- and chloride-dependent GABA transporter 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
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent GABA transporter 2 1
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent GABA transporter 1 1

Data from ChEMBL 36 via Core Engine