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Compound Detail

CHEMBL47009

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O=C(O)CCC(CP(=O)(O)O)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL47009
Phase Preclinical
Structure Type MOL
InChI Key ISEYJGQFXSTPMQ-UHFFFAOYSA-N
5
Targets
26
Activities
4
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

226.1
MW (Da)
-0.27
ALogP
3
HBA
4
HBD
132.1
PSA (Ų)
0.46
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C6H11O7P
MW 226.12
Aromatic Rings 0
Heavy Atoms 14
NP-Likeness 0.86

Activity Summary

IC50 12 meas. best 9.52
Ki 10 meas. best 9.7
EC50 2 meas. best 9.21
Kd 2 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate carboxypeptidase 2
CHEMBL1892
 Ki 9.7 9.08 0.2 7
Glutamate carboxypeptidase 2
CHEMBL5098
 Ki 9.56 9.56 0.3 1
Glutamate carboxypeptidase 2
CHEMBL1892
 IC50 9.52 8.4122 0.3 9
Glutamate carboxypeptidase 2
CHEMBL5098
 IC50 9.52 8.905 0.3 2
Unchecked
CHEMBL612545
 IC50 9.52 9.52 0.3 1
Glutamate carboxypeptidase 2
CHEMBL1892
 Kd 9.4 9.35 0.4 2
Glutamate carboxypeptidase 2
CHEMBL1892
 EC50 9.21 9.21 0.6 1
Rattus norvegicus
CHEMBL376
 EC50 8.92 8.92 1.2 1
N-acetylated-alpha-linked acidic dipeptidase 2
CHEMBL2609
 Ki 8.85 8.85 1.4 1
Unchecked
CHEMBL612545
 Ki 8.57 8.57 2.7 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 438.67 ng.hr.mL-1 Mus musculus
AUC 135.67 ng.hr.mL-1 Mus musculus
Cmax 860.0 nM Mus musculus
Cmax 280.0 nM Mus musculus
Tmax 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutamate carboxypeptidase 2 Ki = 0.2 nM 9.7 Inhibitory concentration required against Glutamate carboxypeptidase II 12798312
Glutamate carboxypeptidase 2 Ki = 0.2 nM 9.7 In vitro inhibitory activity against glutamate carboxypeptidase II (GCP II) usin... 12723961
Glutamate carboxypeptidase 2 Ki = 0.275 nM 9.56 Compound was tested for inhibition of the Folate hydrolase 8558536
Glutamate carboxypeptidase 2 Ki = 0.28 nM 9.55 Inhibition of antiTEV-tagged GCP2 extracellular portion (aa 44-750) (unknown ori... 25923815
Glutamate carboxypeptidase 2 IC50 = 0.3 nM 9.52 Inhibition of Glutamate carboxypeptidase II 12798312
Glutamate carboxypeptidase 2 IC50 = 0.3 nM 9.52 Inhibition of N-acetyl-L-aspartyl-[3H]L-glutamate binding to glutamate carboxype... 12723961
Glutamate carboxypeptidase 2 IC50 = 0.3 nM 9.52 Inhibitory concentration against rat brain NAALADase (Folate hydrolase) 11708918
Unchecked IC50 = 0.3 nM 9.52 In vitro inhibition of N-acetyl-L-aspartyl-[3H]L-glutamate binding to Glutamate ... 15801825
Glutamate carboxypeptidase 2 IC50 = 0.3 nM 9.52 Inhibition of human recombinant NAALADase 18060794
Glutamate carboxypeptidase 2 IC50 = 0.3 nM 9.52 Inhibition of GCP-2 (unknown origin) 22949627
Glutamate carboxypeptidase 2 Ki = 0.3 nM 9.52 Binding affinity to NAALADase 23025786
Glutamate carboxypeptidase 2 Ki = 0.4 nM 9.4 Inhibition of NAALADase activity in human LNCaP cell membranes assessed as inhib... 23025786
Glutamate carboxypeptidase 2 Kd = 0.4 nM 9.4 Binding affinity to PSMA in human LNCaP cells assessed as cell surface binding i... 19108655
Glutamate carboxypeptidase 2 Kd = 0.5 nM 9.3 Binding affinity to PSMA in human PC3 cells assessed as cell surface binding in ... 19108655
Glutamate carboxypeptidase 2 EC50 = 0.62 nM 9.21 Concentration required for the neuroprotective effect determined by inhibition o... 12798312
Glutamate carboxypeptidase 2 IC50 = 1.1 nM 8.96 Inhibition of NAALADase activity in human LNCaP cell membranes assessed as inhib... 23025786
Rattus norvegicus EC50 = 1.2 nM 8.92 Neuroprotective effect against ischemic injury with median effective concentrati... 15801825
N-acetylated-alpha-linked acidic dipeptidase 2 Ki = 1.4 nM 8.85 In vitro inhibitory activity against human Glutamate carboxypeptidase II by usin... 15027864
Unchecked Ki = 2.7 nM 8.57 Inhibition of antiTEV-tagged GCP3 extracellular portion (aa 36-740) (unknown ori... 25923815
Glutamate carboxypeptidase 2 IC50 = 5.1 nM 8.29 Inhibitory activity against expressed rat Glutamate carboxypeptidase II, using a... 11462970

Literature References

PubMed DOI Target Context # Activities
26930119 10.1021/acs.jmedchem.6b00062 Plasma 8
8558536 10.1021/jm950801q Rattus norvegicus 6
26930119 10.1021/acs.jmedchem.6b00062 Mus musculus 5
23025786 10.1021/jm300710j Glutamate carboxypeptidase 2 3
12798312 10.1016/s0960-894x(03)00407-4 Glutamate carboxypeptidase 2 3
19108655 10.1021/jm801033c Glutamate carboxypeptidase 2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
25923815 10.1021/acs.jmedchem.5b00278 Unchecked 2
12723961 10.1021/jm020515w Glutamate carboxypeptidase 2 2
15801825 10.1021/jm049258g Rattus norvegicus 1
18060794 10.1016/j.bmc.2007.11.030 Glutamate carboxypeptidase 2 1
15801825 10.1021/jm049258g Unchecked 1
8558536 10.1021/jm950801q Glutamate carboxypeptidase 2 1
24063417 10.1021/jm400895s Glutamate carboxypeptidase 2 1
22949627 10.1124/dmd.112.046821 Glutamate carboxypeptidase 2 1
25923815 10.1021/acs.jmedchem.5b00278 Glutamate carboxypeptidase 2 1
11708918 10.1021/jm0001774 Glutamate carboxypeptidase 2 1
26894427 10.1021/acs.jmedchem.5b01881 Glutamate carboxypeptidase 2 1
37465305 10.1021/acsmedchemlett.3c00087 Glutamate carboxypeptidase 2 1
15027864 10.1021/jm0306226 N-acetylated-alpha-linked acidic dipeptidase 2 1

Data from ChEMBL 36 via Core Engine