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Compound Detail

CHEMBL450938

(3-NITROPHENYLAMINO)METHYLENEDIPHOSPHONIC ACID
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O=[N+]([O-])c1cccc(NC(P(=O)(O)O)P(=O)(O)O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL450938
Name (3-NITROPHENYLAMINO)METHYLENEDIPHOSPHONIC ACID
Phase Preclinical
Structure Type MOL
InChI Key VPXZTOOBAWPNGR-UHFFFAOYSA-N
7
Targets
11
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

312.1
MW (Da)
0.65
ALogP
5
HBA
5
HBD
170.2
PSA (Ų)
0.30
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C7H10N2O8P2
MW 312.11
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.96

Activity Summary

IC50 11 meas. best 7.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Carbonic anhydrase 12
CHEMBL3242
 IC50 7.06 7.06 88.0 1
Carbonic anhydrase 1
CHEMBL261
 IC50 6.09 6.09 814.0 1
Hexokinase
CHEMBL4151
 IC50 6.09 5.7767 810.0 3
Glutamine synthetase
CHEMBL2366486
 IC50 5.7 5.7 1990.0 1
Vacuolar-type proton translocating pyrophosphatase 1
CHEMBL4386
 IC50 5.19 5.19 6500.0 1
72 kDa type IV collagenase
CHEMBL333
 IC50 4.81 4.81 15500.0 1
Dictyostelium discoideum
CHEMBL612373
 IC50 4.11 4.11 78000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Carbonic anhydrase 12 IC50 = 88.0 nM 7.06 Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins b... 24650641
Hexokinase IC50 = 810.0 nM 6.09 Inhibition of Trypanosoma cruzi hexokinase 17329254
Carbonic anhydrase 1 IC50 = 814.0 nM 6.09 Inhibition of human recombinant carbonic anhydrase 1 preincubated for 15 mins by... 24650641
Glutamine synthetase IC50 = 1990.0 nM 5.7 Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase by... 15161194
Hexokinase IC50 = 2400.0 nM 5.62 Inhibitory activity against Trypanosoma cruzi hexokinase 16392806
Hexokinase IC50 = 2398.83 nM 5.62 Inhibitory activity against Trypanosoma cruzi hexokinase 16392806
Vacuolar-type proton translocating pyrophosphatase 1 IC50 = 6500.0 nM 5.19 Inhibition of recombinant Trypanosoma brucei soluble vacuolar pyrophosphatase ex... 16162013
72 kDa type IV collagenase IC50 = 15500.0 nM 4.81 Inhibition of APMA-activated recombinant human MMP2 using Mca-Pro-Leu-Gly-Leu-Dp... 24071448
Dictyostelium discoideum IC50 = 78000.0 nM 4.11 Cytotoxicity to Dictyostelium discoideum 16392806

Literature References

PubMed DOI Target Context # Activities
15161194 10.1021/jf049843q Glutamine synthetase 6
16392806 10.1021/jm0582625 Hexokinase 2
17474756 10.1021/jf0701032 Pyrroline-5-carboxylate reductase 2
24650641 10.1016/j.bmcl.2014.03.001 Carbonic anhydrase 14 1
16162013 10.1021/jm058220g Vacuolar-type proton translocating pyrophosphatase 1 1
24650641 10.1016/j.bmcl.2014.03.001 Carbonic anhydrase 12 1
24650641 10.1016/j.bmcl.2014.03.001 Carbonic anhydrase 9 1
24650641 10.1016/j.bmcl.2014.03.001 Carbonic anhydrase 2 1
24650641 10.1016/j.bmcl.2014.03.001 Carbonic anhydrase 1 1
24071448 10.1016/j.bmc.2013.08.054 72 kDa type IV collagenase 1
24071448 10.1016/j.bmc.2013.08.054 Neutrophil collagenase 1
24071448 10.1016/j.bmc.2013.08.054 Matrix metalloproteinase-9 1
24071448 10.1016/j.bmc.2013.08.054 Matrix metalloproteinase-14 1
24071448 10.1016/j.bmc.2013.08.054 Hydroxyapatite 1
24071448 10.1016/j.bmc.2013.08.054 NON-PROTEIN TARGET 1
24071448 10.1016/j.bmc.2013.08.054 HepG2 1
17329254 10.1074/jbc.m607286200 Hexokinase 1
16392806 10.1021/jm0582625 ADMET 1
16392806 10.1021/jm0582625 Dictyostelium discoideum 1
16392806 10.1021/jm0582625 KB 1

Data from ChEMBL 36 via Core Engine