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Compound Detail

CHEMBL3114672

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COc1cc(C(O)P(=O)(O)CC[C@H](N)C(=O)O)cc([N+](=O)[O-])c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3114672
Phase Preclinical
Structure Type MOL
InChI Key PEXVMHLARUAHNC-KAJCPDDVSA-N
6
Targets
14
Activities
2
Assay Types
17
PK Parameters
19
Publications
0
Known Names

Molecular Properties

364.2
MW (Da)
0.37
ALogP
8
HBA
5
HBD
193.4
PSA (Ų)
0.24
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C12H17N2O9P
MW 364.25
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 0.34

Activity Summary

EC50 11 meas. best 6.7
IC50 3 meas. best 5.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Metabotropic glutamate receptor 4
CHEMBL4105794
 EC50 6.7 6.7 200.0 1
Metabotropic glutamate receptor 4
CHEMBL2736
 EC50 6.05 5.8433 900.0 3
Metabotropic glutamate receptor 6
CHEMBL4573
 EC50 5.77 5.635 1700.0 2
Metabotropic glutamate receptor 4
CHEMBL2736
 IC50 5.07 5.07 8600.0 1
Metabotropic glutamate receptor 8
CHEMBL3228
 EC50 4.71 4.445 19400.0 2
Metabotropic glutamate receptor 4
CHEMBL2787
 EC50 4.7 4.7 20000.0 1
Metabotropic glutamate receptor 7
CHEMBL3777
 EC50 4.28 4.28 53000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 200.0 ng.hr.mL-1 Rattus norvegicus
AUC 2800.0 ng.hr.mL-1 Rattus norvegicus
AUC 3500.0 ng.hr.mL-1 Rattus norvegicus
AUC 0.7 ug.hr/g Rattus norvegicus
AUC 30000.0 ng.hr.mL-1 Rattus norvegicus
CL 6.2 mL.min-1.kg-1 Rattus norvegicus
Cmax 252.57 nM Rattus norvegicus
F 0.8 % Rattus norvegicus
Fu 253.0 nM Rattus norvegicus
Fu 0.99 - Mus musculus
Fu 0.99 - Rattus norvegicus
Fu 0.99 - Mus musculus
Fu 0.99 - Rattus norvegicus
Fu 0.73 - Homo sapiens
T1/2 0.3 hr Rattus norvegicus
T1/2 0.3333 hr Rattus norvegicus
Tmax 1.4 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Metabotropic glutamate receptor 4 EC50 = 200.0 nM 6.7 Agonist activity at mGlu4 in C57/Bl6 mouse GP neurons assessed as inhibition of ... 29397723
Metabotropic glutamate receptor 4 EC50 = 900.0 nM 6.05 Agonist activity at mGlu4 (unknown origin) expressed in HEK293 cells coexpressin... 29397723
Metabotropic glutamate receptor 4 EC50 = 1500.0 nM 5.82 Agonist activity at human mGlu4 receptor by FLIPR assay relative to control 24900783
Metabotropic glutamate receptor 6 EC50 = 1700.0 nM 5.77 Agonist activity at mGlu6 (unknown origin) expressed in HEK293 cells coexpressin... 29397723
Metabotropic glutamate receptor 4 EC50 = 2200.0 nM 5.66 Agonist activity at mGlu4 (unknown origin) expressed in HEK293 cells coexpressin... 29397723
Metabotropic glutamate receptor 6 EC50 = 3200.0 nM 5.5 Agonist activity at mGlu6 (unknown origin) expressed in HEK293 cells coexpressin... 29397723
Metabotropic glutamate receptor 4 IC50 = 8600.0 nM 5.07 Displacement of [3H]-L-AP4 from human mGlu4 receptor 24900783
Metabotropic glutamate receptor 8 EC50 = 19400.0 nM 4.71 Agonist activity at mGlu8 (unknown origin) expressed in HEK293 cells coexpressin... 29397723
Metabotropic glutamate receptor 4 EC50 = 20000.0 nM 4.7 Agonist activity at mGlu4 assessed as decrease in PF-induced presynaptic calcium... 29397723
Metabotropic glutamate receptor 7 EC50 = 53000.0 nM 4.28 Agonist activity at mGlu7 (unknown origin) expressed in HEK293 cells coexpressin... 29397723
Metabotropic glutamate receptor 8 EC50 = 66000.0 nM 4.18 Agonist activity at mGlu8 (unknown origin) expressed in HEK293 cells coexpressin... 29397723

Literature References

PubMed DOI Target Context # Activities
29397723 10.1021/acs.jmedchem.7b01438 Metabotropic glutamate receptor 4 12
24900783 10.1021/ml400338f Rattus norvegicus 9
24900783 10.1021/ml400338f Plasma 9
24900783 10.1021/ml400338f ADMET 6
24900783 10.1021/ml400338f Brain 6
24900783 10.1021/ml400338f Unchecked 3
24900783 10.1021/ml400338f No relevant target 3
24900783 10.1021/ml400338f Metabotropic glutamate receptor 4 3
29397723 10.1021/acs.jmedchem.7b01438 Unchecked 2
29397723 10.1021/acs.jmedchem.7b01438 Metabotropic glutamate receptor 7 2
29397723 10.1021/acs.jmedchem.7b01438 Metabotropic glutamate receptor 6 2
29397723 10.1021/acs.jmedchem.7b01438 Metabotropic glutamate receptor 8 2
24900783 10.1021/ml400338f MDCK 2
24900783 10.1021/ml400338f Liver microsome 2
24900783 10.1021/ml400338f Voltage-gated inwardly rectifying potassium channel KCNH2 1
24900783 10.1021/ml400338f NON-PROTEIN TARGET 1
29397723 10.1021/acs.jmedchem.7b01438 Glutamate NMDA receptor; Grin1/Grin2a 1
29397723 10.1021/acs.jmedchem.7b01438 Ionotropic glutamate receptor NMDA1/2B 1
24900783 10.1021/ml400338f HepG2 1

Data from ChEMBL 36 via Core Engine