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Compound Detail

CHEMBL55518

(3,5-DICHLOROPHENYLAMINO)METHYLENEDIPHOSPHONIC ACID
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O=P(O)(O)C(Nc1cc(Cl)cc(Cl)c1)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL55518
Name (3,5-DICHLOROPHENYLAMINO)METHYLENEDIPHOSPHONIC ACID
Phase Preclinical
Structure Type MOL
InChI Key ALPQLQJFTUXTFT-UHFFFAOYSA-N
5
Targets
18
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

336.0
MW (Da)
2.04
ALogP
3
HBA
5
HBD
127.1
PSA (Ų)
0.53
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 C7H9Cl2NO6P2
MW 336.00
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.56

Activity Summary

IC50 13 meas. best 7.11
Ki 5 meas. best 5.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Pyrroline-5-carboxylate reductase
CHEMBL2242730
 IC50 7.11 5.11 77.0 3
Glutamine synthetase
CHEMBL2366486
 IC50 6.4 4.855 396.0 4
Glutamine synthetase, chloroplastic
CHEMBL2285357
 Ki 5.19 5.165 6400.0 2
Glutamine synthetase, chloroplastic
CHEMBL2285357
 IC50 5.12 5.12 7600.0 2
Pyrroline-5-carboxylate reductase
CHEMBL2242730
 Ki 4.99 4.99 10300.0 1
Glutamine synthetase
CHEMBL2366402
 IC50 4.52 4.52 30000.0 1
Glutamine synthetase
CHEMBL2366496
 IC50 4.52 4.52 30000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Pyrroline-5-carboxylate reductase IC50 = 77.0 nM 7.11 Inhibition of Arabidopsis thaliana P5C reductase catalytic activity 17474756
Glutamine synthetase IC50 = 396.0 nM 6.4 Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase by... 15161194
Glutamine synthetase, chloroplastic Ki = 6400.0 nM 5.19 Un-competitive inhibition of Zea mays cv. Jeff (maize) leaf glutamine synthetase... 19697446
Glutamine synthetase, chloroplastic Ki = 7200.0 nM 5.14 Non-competitive inhibition of Zea mays cv. Jeff( maize) leaf glutamine synthetas... 19697446
Glutamine synthetase, chloroplastic IC50 = 7603.26 nM 5.12 Inhibition of Zea mays cv. Jeff (maize) leaf glutamine synthetase using L-glutam... 19697446
Glutamine synthetase, chloroplastic IC50 = 7600.0 nM 5.12 Inhibition of Zea mays cv. Jeff (maize) leaf glutamine synthetase using L-glutam... 19697446
Pyrroline-5-carboxylate reductase Ki = 10300.0 nM 4.99 Uncompetitive inhibition of Arabidopsis thaliana P5C reductase by Dixon plot 17474756
Glutamine synthetase IC50 = 30000.0 nM 4.52 Inhibition of glutamine synthetase in Nicotiana tabacum (tobacco) cells 17474756
Glutamine synthetase IC50 = 30000.0 nM 4.52 Inhibition of Spinacia oleracea (spinach) glutamine synthetase activity 17474756
Glutamine synthetase IC50 = 33000.0 nM 4.48 Inhibition of Oryza sativa (rice) glutamine synthetase 18399639
Glutamine synthetase IC50 = 33000.0 nM 4.48 Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase as... 15161194
Pyrroline-5-carboxylate reductase IC50 = 77000.0 nM 4.11 Inhibition of Arabidopsis thaliana P5C assessed as reduction in NADH oxidation i... 18399639
Pyrroline-5-carboxylate reductase IC50 = 76913.04 nM 4.11 Inhibition of Arabidopsis thaliana P5C assessed as reduction in NADH oxidation i... 18399639
Glutamine synthetase IC50 = 88000.0 nM 4.06 Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase af... 15161194

Literature References

PubMed DOI Target Context # Activities
15161194 10.1021/jf049843q Glutamine synthetase 7
17474756 10.1021/jf0701032 Pyrroline-5-carboxylate reductase 6
15161194 10.1021/jf049843q Oryza sativa 6
19697446 10.1002/ps.1830 Glutamine synthetase, chloroplastic 5
18399639 10.1021/jf800029t Arabidopsis thaliana 4
17149863 10.1021/jm060492b Escherichia coli 3
18399639 10.1021/jf800029t Pyrroline-5-carboxylate reductase 2
17474756 10.1021/jf0701032 Glutamine synthetase 2
14695831 10.1021/jm030084x Entamoeba histolytica 1
14695831 10.1021/jm030084x Plasmodium falciparum 1
14695831 10.1021/jm030084x KB 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
20185316 10.1016/j.bmc.2010.01.068 Entamoeba histolytica 1
18399639 10.1021/jf800029t Glutamine synthetase 1

Data from ChEMBL 36 via Core Engine