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Compound Detail

CHEMBL3616847

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N[C@@]1(C(=O)O)C[C@@H](Sc2nnc[nH]2)[C@H]2[C@H](C(=O)O)[C@H]21

Basic Information

ChEMBL ID CHEMBL3616847
Phase Preclinical
Structure Type MOL
InChI Key YSOWRGMLMZQSBX-AVUIYAGVSA-N
4
Targets
17
Activities
3
Assay Types
26
PK Parameters
19
Publications
0
Known Names

Molecular Properties

284.3
MW (Da)
-0.60
ALogP
6
HBA
4
HBD
142.2
PSA (Ų)
0.57
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C10H12N4O4S
MW 284.30
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.06

Activity Summary

EC50 13 meas. best 8.25
IC50 2 meas. best 5.56
Ki 2 meas. best 6.84

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Metabotropic glutamate receptor 2
CHEMBL5137
EC50 8.25 7.6567 5.6 6
Metabotropic glutamate receptor 3
CHEMBL2888
EC50 6.89 5.856 129.0 5
Metabotropic glutamate receptor 2
CHEMBL5137
Ki 6.84 6.84 144.0 1
Metabotropic glutamate receptor 3
CHEMBL2888
Ki 6.81 6.81 156.0 1
Metabotropic glutamate receptor 3
CHEMBL2888
IC50 5.56 5.08 2730.0 2
Metabotropic glutamate receptor 6
CHEMBL4573
EC50 5.46 5.46 3450.0 1
Metabotropic glutamate receptor 8
CHEMBL3228
EC50 5.0 5.0 10100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 12253.33 ng.hr.mL-1 Rattus norvegicus
AUC 3070.44 ng.hr.mL-1 Rattus norvegicus
AUC 1708.64 ng.hr.mL-1 Rattus norvegicus
AUC 287.14 ng.hr.mL-1 Rattus norvegicus
AUC 1395.91 ng.hr.mL-1 Rattus norvegicus
CL 12.3 mL.min-1.kg-1 Rattus norvegicus
Cmax 31100.0 nM Rattus norvegicus
Cmax 8050.0 nM Rattus norvegicus
Cmax 4920.0 nM Rattus norvegicus
Cmax 220.0 nM Rattus norvegicus
Cmax 9540.0 nM Rattus norvegicus
F 88.0 % Rattus norvegicus
F 73.0 % Rattus norvegicus
F 122.0 % Rattus norvegicus
F 4.0 % Rattus norvegicus
Fu 0.98 - Homo sapiens
Fu 0.98 - Rattus norvegicus
T1/2 5.2 hr Rattus norvegicus
T1/2 3.2 hr Rattus norvegicus
T1/2 1.2 hr Rattus norvegicus
T1/2 3.7 hr Rattus norvegicus
T1/2 3.3 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus
Tmax 0.33 hr Rattus norvegicus
Tmax 0.4 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Metabotropic glutamate receptor 2 EC50 = 5.6 nM 8.25 Agonist activity at human recombinant mGlu2 receptor expressed in AV12 cells ass... 26313429
Metabotropic glutamate receptor 2 EC50 = 20.1 nM 7.7 Agonist activity at wild type human recombinant mGlu2 receptor expressed in AV12... 26313429
Metabotropic glutamate receptor 2 EC50 = 21.1 nM 7.68 Agonist activity at human recombinant mGlu2 receptor expressed in AV12 cells ass... 26313429
Metabotropic glutamate receptor 2 EC50 = 22.1 nM 7.66 Agonist activity at human recombinant mGlu2 receptor L300Q mutant expressed in A... 26313429
Metabotropic glutamate receptor 2 EC50 = 46.3 nM 7.33 Agonist activity at human recombinant mGlu2 receptor E273D mutant expressed in A... 26313429
Metabotropic glutamate receptor 2 EC50 = 48.2 nM 7.32 Agonist activity at human recombinant mGlu2 receptor E273D and L300Q mutant expr... 26313429
Metabotropic glutamate receptor 3 EC50 = 129.0 nM 6.89 Agonist activity at human recombinant mGlu3 receptor expressed in AV12 cells ass... 26313429
Metabotropic glutamate receptor 2 Ki = 144.0 nM 6.84 Displacement of [3H]-459477 from human recombinant mGlu2 receptor expressed in A... 26313429
Metabotropic glutamate receptor 3 Ki = 156.0 nM 6.81 Displacement of [3H]-459477 from human recombinant mGlu3 receptor expressed in A... 26313429
Metabotropic glutamate receptor 3 EC50 = 1175.0 nM 5.93 Agonist activity at human recombinant mGlu3 receptor D279E and Q306L mutant expr... 26313429
Metabotropic glutamate receptor 3 EC50 = 2181.0 nM 5.66 Agonist activity at human recombinant mGlu3 receptor D279E mutant expressed in A... 26313429
Metabotropic glutamate receptor 3 IC50 = 2730.0 nM 5.56 Antagonist activity at human recombinant mGlu3 receptor expressed in AV12 cells ... 26313429
Metabotropic glutamate receptor 3 EC50 = 2831.0 nM 5.55 Agonist activity at human recombinant mGlu3 receptor Q306L mutant expressed in A... 26313429
Metabotropic glutamate receptor 6 EC50 = 3450.0 nM 5.46 Agonist activity at human recombinant mGlu6 receptor expressed in AV12 cells ass... 26313429
Metabotropic glutamate receptor 3 EC50 = 5676.0 nM 5.25 Agonist activity at wild type human recombinant mGlu3 receptor expressed in AV12... 26313429
Metabotropic glutamate receptor 8 EC50 = 10100.0 nM 5.0 Agonist activity at human recombinant mGlu8 receptor expressed in AV12 cells ass... 26313429
Metabotropic glutamate receptor 3 IC50 = 25200.0 nM 4.6 Antagonist activity at human recombinant mGlu3 receptor expressed in AV12 cells ... 26313429

Literature References

PubMed DOI Target Context # Activities
26313429 10.1021/acs.jmedchem.5b01124 Rattus norvegicus 31
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 2 22
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 3 16
26313429 10.1021/acs.jmedchem.5b01124 Plasma 11
26313429 10.1021/acs.jmedchem.5b01124 Cerebrospinal fluid 9
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 8 4
26313429 10.1021/acs.jmedchem.5b01124 Unchecked 4
26313429 10.1021/acs.jmedchem.5b01124 ADMET 3
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 7 2
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 6 2
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 5 2
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 4 2
26313429 10.1021/acs.jmedchem.5b01124 No relevant target 2
26313429 10.1021/acs.jmedchem.5b01124 Metabotropic glutamate receptor 1 2
26313429 10.1021/acs.jmedchem.5b01124 Voltage-gated inwardly rectifying potassium channel KCNH2 1
26313429 10.1021/acs.jmedchem.5b01124 Cytochrome P450 2C9 1
26313429 10.1021/acs.jmedchem.5b01124 Cytochrome P450 2D6 1
26313429 10.1021/acs.jmedchem.5b01124 Cytochrome P450 3A4 1
26313429 10.1021/acs.jmedchem.5b01124 Hepatocyte 1

Data from ChEMBL 36 via Core Engine