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Compound Detail

CHEMBL39071

ISOGUVACINE
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O=C(O)C1=CCNCC1

Basic Information

ChEMBL ID CHEMBL39071
Name ISOGUVACINE
Phase Preclinical
Structure Type MOL
InChI Key KRVDMABBKYMBHG-UHFFFAOYSA-N
12
Targets
26
Activities
3
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

EC50 21 meas. best 6.11
Ki 3 meas. best 7.26
IC50 2 meas. best 7.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; anion channel
CHEMBL1907607
IC50 7.66 6.985 22.0 2
GABA-A receptor; anion channel
CHEMBL2093872
Ki 7.26 7.26 55.0 2
Unchecked
CHEMBL612545
EC50 6.11 5.46 780.0 3
GABA-A receptor; anion channel
CHEMBL1907607
EC50 5.51 5.51 3100.0 1
GABA A receptor alpha-2/beta-2/gamma-2
CHEMBL2111413
EC50 5.35 5.35 4466.8 2
GABA A receptor alpha-3/beta-2/gamma-2
CHEMBL2111339
EC50 5.25 5.25 5600.0 2
GABA-A receptor; alpha-1/beta-2/gamma-2
CHEMBL2095172
EC50 4.96 4.955 11000.0 2
Rattus norvegicus
CHEMBL376
EC50 4.89 4.89 13000.0 1
GABA-A receptor; alpha-6/beta-3/gamma-2
CHEMBL2095190
EC50 4.7 4.7 20000.0 1
Gamma-aminobutyric acid receptor subunit rho-1
CHEMBL3561
EC50 4.41 4.41 38904.5 2
GABA-A receptor; alpha-2/beta-3/gamma-2
CHEMBL2094130
EC50 4.3 4.3 50000.0 1
GABA-A receptor; alpha-3/beta-3/gamma-2
CHEMBL2094120
EC50 4.26 4.26 55000.0 1
GABA-A receptor; alpha-5/beta-3/gamma-2
CHEMBL2094122
EC50 4.12 4.12 75000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; anion channel IC50 = 22.0 nM 7.66 Binding affinity against Gamma-aminobutyric acid A receptor in rat cerebral cort... 7650683
GABA-A receptor; anion channel Ki = 55.0 nM 7.26 Displacement of [3H]muscimol from GABAA receptor in SPRD rat brain synaptic memb... 25038482
GABA-A receptor; anion channel Ki = 54.95 nM 7.26 Displacement of [3H]muscimol from GABAA receptor in SPRD rat brain synaptic memb... 25038482
GABA-A receptor; anion channel IC50 = 490.0 nM 6.31 Inhibition of [3H]-GABA binding to GABA-A receptor in rat cerebral cortex homoge... -
Unchecked EC50 = 780.0 nM 6.11 Agonist activity at human GABAAalpha5beta2gamma2S receptor expressed in tsA-201c... 25038482
Unchecked EC50 = 794.33 nM 6.1 Agonist activity at human GABAAalpha5beta2gamma2S receptor expressed in tsA-201c... 25038482
GABA-A receptor; anion channel EC50 = 3100.0 nM 5.51 Effective concentration for stimulation of [3H]diazepam binding to rat cortical ... -
GABA A receptor alpha-2/beta-2/gamma-2 EC50 = 4466.84 nM 5.35 Agonist activity at human GABAAalpha2beta2gamma2S receptor expressed in tsA-201c... 25038482
GABA A receptor alpha-2/beta-2/gamma-2 EC50 = 4500.0 nM 5.35 Agonist activity at human GABAAalpha2beta2gamma2S receptor expressed in tsA-201c... 25038482
GABA A receptor alpha-3/beta-2/gamma-2 EC50 = 5623.41 nM 5.25 Agonist activity at human GABAAalpha3beta2gamma2S receptor expressed in tsA-201c... 25038482
GABA A receptor alpha-3/beta-2/gamma-2 EC50 = 5600.0 nM 5.25 Agonist activity at human GABAAalpha3beta2gamma2S receptor expressed in tsA-201c... 25038482
GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 = 11000.0 nM 4.96 Agonist activity at human GABAAalpha1beta2gamma2S receptor expressed in tsA-201c... 25038482
GABA-A receptor; alpha-1/beta-2/gamma-2 EC50 = 11220.18 nM 4.95 Agonist activity at human GABAAalpha1beta2gamma2S receptor expressed in tsA-201c... 25038482
Rattus norvegicus EC50 = 13000.0 nM 4.89 Tested for inhibition of CA1 population spike in rat hippocampal slice by electr... -
GABA-A receptor; alpha-6/beta-3/gamma-2 EC50 = 20000.0 nM 4.7 Effective agonist dose for human Gamma-aminobutyric acid A receptor alpha-6-beta... 11412984
Gamma-aminobutyric acid receptor subunit rho-1 EC50 = 39000.0 nM 4.41 Agonist activity at human GABAA rho1 expressed in tsA-201cells by FLIPR membrane... 25038482
Gamma-aminobutyric acid receptor subunit rho-1 EC50 = 38904.51 nM 4.41 Agonist activity at human GABAA rho1 expressed in tsA-201cells by FLIPR membrane... 25038482
GABA-A receptor; alpha-2/beta-3/gamma-2 EC50 = 50000.0 nM 4.3 Agonist activity on human Gamma-aminobutyric acid A receptor alpha-2-beta-3-gamm... 11412984
GABA-A receptor; alpha-3/beta-3/gamma-2 EC50 = 55000.0 nM 4.26 Agonist activity on human Gamma-aminobutyric acid A receptor alpha-3-beta-3-gamm... 11412984
Unchecked EC50 = 67000.0 nM 4.17 Agonist activity at human GABAC rho 1 receptor expressed in HEK293 cells by FMP ... 17655213

Literature References

PubMed DOI Target Context # Activities
25038482 10.1016/j.ejmech.2014.07.039 Gamma-aminobutyric acid receptor subunit rho-1 3
25038482 10.1016/j.ejmech.2014.07.039 Unchecked 3
17655213 10.1021/jm070447j Unchecked 3
25038482 10.1016/j.ejmech.2014.07.039 GABA A receptor alpha-3/beta-2/gamma-2 3
- 10.1016/S0960-894X(01)81035-0 GABA-A receptor; anion channel 3
25038482 10.1016/j.ejmech.2014.07.039 GABA A receptor alpha-2/beta-2/gamma-2 3
11412984 10.1016/s0960-894x(01)00184-6 GABA-A receptor; alpha-1/beta-3/gamma-2 2
25038482 10.1016/j.ejmech.2014.07.039 GABA-A receptor; alpha-1/beta-2/gamma-2 2
25038482 10.1016/j.ejmech.2014.07.039 GABA-A receptor; anion channel 2
21955456 10.1016/j.bmc.2011.08.058 Proton-coupled amino acid transporter 1 2
11412984 10.1016/s0960-894x(01)00184-6 GABA-A receptor; alpha-6/beta-3/gamma-2 2
11412984 10.1016/s0960-894x(01)00184-6 GABA-A receptor; alpha-5/beta-3/gamma-2 2
11412984 10.1016/s0960-894x(01)00184-6 GABA A receptor alpha-4/beta-3/gamma-2 2
11412984 10.1016/s0960-894x(01)00184-6 GABA-A receptor; alpha-3/beta-3/gamma-2 2
11412984 10.1016/s0960-894x(01)00184-6 GABA-A receptor; alpha-2/beta-3/gamma-2 2
7650683 10.1021/jm00017a014 No relevant target 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
7650683 10.1021/jm00017a014 Unchecked 1

Data from ChEMBL 36 via Core Engine