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Compound Detail

CHEMBL204106

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O=CN(O)CCC(c1ccc(Cl)c(Cl)c1)P(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL204106
Phase Preclinical
Structure Type MOL
InChI Key AJGPMMOCRYQLNY-UHFFFAOYSA-N
4
Targets
16
Activities
3
Assay Types
3
PK Parameters
12
Publications
0
Known Names

Molecular Properties

328.1
MW (Da)
2.45
ALogP
3
HBA
3
HBD
98.1
PSA (Ų)
0.32
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 C10H12Cl2NO5P
MW 328.09
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.25

Activity Summary

IC50 8 meas. best 7.55
Ki 7 meas. best 7.82
Kd 1 meas. best 6.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 7.82 7.095 15.0 6
Plasmodium falciparum
CHEMBL364
 IC50 7.55 6.905 28.0 4
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL4091
 IC50 7.23 7.23 59.0 2
Unchecked
CHEMBL612545
 IC50 7.23 7.025 59.0 2
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL5630
 Kd 6.92 6.92 120.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL5630
 Ki 5.92 5.92 1200.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 3.03 10'6/M Escherichia coli
Ka 3.13 10'6/M Plasmodium falciparum
Ka 2.08 10'6/M Mycobacterium tuberculosis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 15.0 nM 7.82 Inhibition of His6-tagged Plasmodium falciparum DXR expressed in Escherichia col... 23050057
Plasmodium falciparum IC50 = 28.0 nM 7.55 Antimalarial activity against Plasmodium falciparum Dd2 16439126
Unchecked Ki = 57.54 nM 7.24 Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 ... 21561155
Unchecked Ki = 58.0 nM 7.24 Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 ... 21561155
Unchecked Ki = 58.0 nM 7.24 Inhibition of Escherichia coli DXR using DXP as substrate preincubated for 5 min... 23050057
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 59.0 nM 7.23 Inhibition of recombinant Escherichia coli DXR 16439126
Unchecked IC50 = 59.0 nM 7.23 Inhibition of Escherichia coli DXR 17583502
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 59.0 nM 7.23 Inhibition of Escherichia coli DXR 21379374
Unchecked Ki = 77.0 nM 7.11 Inhibition of recombinant Toxoplasma gondii DXR catalytic domain (68 to 513) exp... 23428849
Plasmodium falciparum IC50 = 90.0 nM 7.05 Antimalarial activity against Plasmodium falciparum 3D7 16439126
1-deoxy-D-xylulose 5-phosphate reductoisomerase Kd = 120.0 nM 6.92 Binding affinity to Mycobacterium tuberculosis DXR assessed as dissociation cons... 23819803
Unchecked IC50 = 150.0 nM 6.82 Inhibition of Mycobacterium tuberculosis DXR-catalyzed NADPH-dependent rearrange... 21678907
Plasmodium falciparum IC50 = 160.0 nM 6.8 Antiplasmodial activity against Plasmodium falciparum K1 by micro dilution assay 20568776
Plasmodium falciparum IC50 = 600.0 nM 6.22 Antiplasmodial activity against Plasmodium falciparum Ghana by micro dilution as... 20568776
1-deoxy-D-xylulose 5-phosphate reductoisomerase Ki = 1200.0 nM 5.92 Inhibition of Mycobacterium tuberculosis recombinant DXR expressed in Escherichi... 21561155
Unchecked Ki = 1200.0 nM 5.92 Inhibition of Mycobacterium tuberculosis DXR using DXP as substrate preincubated... 23050057

Literature References

PubMed DOI Target Context # Activities
23050057 10.1021/ml300071w Unchecked 6
20568776 10.1021/jm100211e Plasmodium berghei 5
16439126 10.1016/j.bmcl.2005.12.082 Plasmodium falciparum 2
20568776 10.1021/jm100211e Plasmodium falciparum 2
21561155 10.1021/jm200363d Unchecked 2
16439126 10.1016/j.bmcl.2005.12.082 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1
17583502 10.1016/j.bmcl.2007.06.026 Unchecked 1
21379374 10.1021/ml100243r 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1
21561155 10.1021/jm200363d 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1
21678907 10.1021/jm2000085 Unchecked 1
23428849 10.1016/j.bmcl.2013.01.097 Unchecked 1
23819803 10.1021/jm4006498 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1

Data from ChEMBL 36 via Core Engine