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Compound Detail

CHEMBL76768

GUVACINE
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O=C(O)C1=CCCNC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL76768
Name GUVACINE
Phase Preclinical
Structure Type MOL
InChI Key QTDZOWFRBNTPQR-UHFFFAOYSA-N
9
Targets
35
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

127.1
MW (Da)
-0.01
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.52
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 C6H9NO2
MW 127.14
Aromatic Rings 0
Heavy Atoms 9
NP-Likeness 1.42

Activity Summary

IC50 35 meas. best 5.78

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium- and chloride-dependent GABA transporter 1
CHEMBL4054
 IC50 5.78 5.6521 1680.0 14
Rattus norvegicus
CHEMBL376
 IC50 5.31 5.1233 4920.0 3
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 IC50 4.9 4.825 12589.2 4
Sodium- and chloride-dependent GABA transporter 1
CHEMBL1903
 IC50 4.85 4.85 14000.0 2
GABA transporter 4
CHEMBL3699
 IC50 4.59 4.59 25704.0 1
GABA transporter 3
CHEMBL5205
 IC50 4.59 4.365 25704.0 2
Mus musculus
CHEMBL375
 IC50 4.54 4.52 29000.0 2
Sodium- and chloride-dependent GABA transporter 2
CHEMBL4889
 IC50 4.24 4.24 58000.0 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 = 1680.0 nM 5.78 H-bonding interaction between amino acid residue (Tyr-140) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1680.0 nM 5.78 H-bonding interaction between amino acid residue (Asn-137) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1760.0 nM 5.75 H-bonding interaction between amino acid residue (Thr-89) of Sodium- and chlorid... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1870.0 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 = 1850.0 nM 5.73 H-bonding interaction between amino acid residue (Ser-133) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 1910.0 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 = 2260.0 nM 5.65 H-bonding interaction between amino acid residue (Ser-133) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2590.0 nM 5.59 H-bonding interaction between amino acid residue (Tyr-140) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2560.0 nM 5.59 H-bonding interaction between amino acid residue (Asn-137) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2650.0 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 = 2660.0 nM 5.58 H-bonding interaction between amino acid residue (Thr-89) of Sodium- and chlorid... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2770.0 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 = 2790.0 nM 5.55 H-bonding interaction between amino acid residue (Asn-137) of Sodium- and chlori... 15509161
Sodium- and chloride-dependent GABA transporter 1 IC50 = 2900.0 nM 5.54 H-bonding interaction between amino acid residue (Ser-133) of Sodium- and chlori... 15509161
Rattus norvegicus IC50 = 4920.0 nM 5.31 Inhibition of GABA uptake from rat diencephalon-midbrain, 2985785
Rattus norvegicus IC50 = 7300.0 nM 5.14 In vitro inhibition of [3H]GABA uptake in rat Hippocampal slices. 1433224
Rattus norvegicus IC50 = 12000.0 nM 4.92 Inhibition of GABA uptake into crude synaptosomes prepared from adult rat brain 10639282
Sodium- and chloride-dependent GABA transporter 1 IC50 = 12589.25 nM 4.9 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK293 cells after 25 m... 23336362
Sodium- and chloride-dependent GABA transporter 1 IC50 = 13489.63 nM 4.87 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK cells 18395300
Sodium- and chloride-dependent GABA transporter 1 IC50 = 14000.0 nM 4.85 Inhibitory activity against human GABA transporter-1 (hGAT1) 8057281

Literature References

PubMed DOI Target Context # Activities
15509161 10.1021/jm040809c Sodium- and chloride-dependent GABA transporter 1 14
2985785 10.1021/jm50001a020 GABA-A receptor; anion channel 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
23336362 10.1021/jm301800j Sodium- and chloride-dependent GABA transporter 1 2
10639282 10.1021/jm9904452 Mus musculus 2
10639282 10.1021/jm9904452 Rattus norvegicus 1
1433224 10.1021/jm00100a032 Rattus norvegicus 1
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent GABA transporter 1 1
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent GABA transporter 2 1
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent GABA transporter 3 1
8057281 10.1021/jm00041a012 Sodium- and chloride-dependent betaine transporter 1
12873507 10.1016/s0960-894x(03)00535-3 Unchecked 1
2985785 10.1021/jm50001a020 4-aminobutyrate aminotransferase, mitochondrial 1
18395300 10.1016/j.ejmech.2008.01.005 Sodium- and chloride-dependent GABA transporter 1 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 2 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 3 1
18395300 10.1016/j.ejmech.2008.01.005 GABA transporter 4 1
20219271 10.1016/j.ejmech.2010.02.029 Sodium- and chloride-dependent GABA transporter 3 1
20219271 10.1016/j.ejmech.2010.02.029 Sodium- and chloride-dependent GABA transporter 2 1
2985785 10.1021/jm50001a020 Glutamate decarboxylase 1 1

Data from ChEMBL 36 via Core Engine