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Compound Detail

CHEMBL203125

FOSMIDOMYCIN
🧪 Phase III
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🧪 Phase III
O=CN(O)CCCP(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL203125
Name FOSMIDOMYCIN
Phase Phase III
Structure Type MOL
InChI Key GJXWDTUCERCKIX-UHFFFAOYSA-N

Known Names

Fosmidomicina Fosmidomycin Fosmidomycine
10
Targets
68
Activities
4
Assay Types
11
PK Parameters
20
Publications
3
Known Names
2
Indications
1
Mechanisms

Molecular Properties

183.1
MW (Da)
-0.60
ALogP
3
HBA
3
HBD
98.1
PSA (Ų)
0.23
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem fos-; -mycin

Extended Properties

Molecular Formula C4H10NO5P
MW 183.10
Aromatic Rings 0
Heavy Atoms 11
NP-Likeness 0.55

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic inhibitor INHIBITOR 1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic ✓ ✓

Indications

Malaria Malaria, Falciparum

Activity Summary

IC50 54 meas. best 7.7
Ki 10 meas. best 7.68
EC50 3 meas. best 6.36
Kd 1 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL4091
 IC50 7.7 7.51 19.9 6
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL4094
 Ki 7.68 7.68 21.0 1
Unchecked
CHEMBL612545
 Ki 7.68 7.43 21.0 8
Unchecked
CHEMBL612545
 IC50 7.52 7.1221 30.0 19
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL5630
 Kd 7.4 7.4 40.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic
CHEMBL4295619
 IC50 7.2 7.2 63.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL2010623
 IC50 7.1 6.695 80.0 2
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL5630
 IC50 7.1 6.8229 80.0 7
1-deoxy-D-xylulose 5-phosphate reductoisomerase, chloroplastic
CHEMBL2285354
 IC50 7.0 7.0 100.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL5630
 Ki 6.85 6.85 140.0 1
Escherichia coli
CHEMBL354
 IC50 6.66 6.66 220.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.54 6.0633 290.0 15
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL3421521
 IC50 6.36 6.36 438.0 1
Plasmodium falciparum
CHEMBL364
 EC50 6.36 6.0833 440.0 3

Pharmacokinetic Data

Parameter Value Units Species
CL 3.02 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 30.0 % Rattus norvegicus
Ka 6.67 10'6/M Escherichia coli
Ka 1.28 10'7/M Plasmodium falciparum
Ka 3.45 10'6/M Mycobacterium tuberculosis
Ka 7.35 10'6/M Escherichia coli
Ka 5.6 10'6/M Escherichia coli
T1/2 1.0 hr -
T1/2 1.0 hr -
T1/2 1.0 hr Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 19.95 nM 7.7 Inhibitory concentration against DOXP reductoisomerase 15887963
Unchecked Ki = 21.0 nM 7.68 Inhibition of His6-tagged Plasmodium falciparum DXR expressed in Escherichia col... 23050057
1-deoxy-D-xylulose 5-phosphate reductoisomerase Ki = 21.0 nM 7.68 Binding affinity against Synechocystis strain PCC6803 DXP reductoisomerase 15454217
Unchecked Ki = 21.0 nM 7.68 Inhibition of Plasmodium falciparum recombinant DXR using DXP as substrate prein... 23795240
Unchecked Ki = 27.0 nM 7.57 Inhibition of Escherichia coli DXR using DXP as substrate preincubated for 5 min... 23050057
Unchecked Ki = 27.0 nM 7.57 Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 ... 21561155
Unchecked Ki = 26.92 nM 7.57 Inhibition of Escherichia coli recombinant DXR using DXP as substrate and MgCl2 ... 21561155
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 30.0 nM 7.52 Inhibition of recombinant Escherichia coli DXR 16439126
Unchecked IC50 = 30.0 nM 7.52 Inhibition of Escherichia coli DXR by spectrophotometric method 17491006
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 30.0 nM 7.52 Inhibition of Escherichia coli DXR 21379374
Unchecked IC50 = 32.0 nM 7.5 Inhibition of Escherichia coli recombinant His6-tagged DXR expressed in Escheric... 23025997
Unchecked IC50 = 32.0 nM 7.5 Inhibition of N-terminal His6-tagged Escherichia coli DXR after 2 mins in presen... 23414808
Unchecked IC50 = 32.0 nM 7.5 Inhibition of Plasmodium falciparum DXR using DXP as substrate measured every 5 ... 23819803
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 32.0 nM 7.5 Inhibition of His-tagged Escherichia coli DXR pre-incubated for 2 mins before re... 24890653
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 32.0 nM 7.5 Inhibition of Escherichia coli Dxr 25210872
Unchecked Ki = 34.0 nM 7.47 Inhibition of Escherichia coli recombinant DXR using DXP as substrate preincubat... 23795240
Unchecked IC50 = 34.0 nM 7.47 Inhibition of Escherichia coli DXR 17583502
Unchecked IC50 = 35.0 nM 7.46 Inhibition of Escherichia coli IspC -
Unchecked IC50 = 36.0 nM 7.44 Inhibition of recombinant Plasmodium falciparum Dxr expressed in Escherichia col... 25781377
1-deoxy-D-xylulose 5-phosphate reductoisomerase Kd = 40.0 nM 7.4 Binding affinity to Mycobacterium tuberculosis DXR assessed as dissociation cons... 23819803

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23050057 10.1021/ml300071w Unchecked 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17149863 10.1021/jm060492b Escherichia coli 7
20568776 10.1021/jm100211e Plasmodium berghei 3
21866890 10.1021/jm200694q Unchecked 3
25633870 10.1021/jm5019719 Plasmodium falciparum 3
25781377 10.1021/jm5014264 Escherichia coli 3
19783991 10.1038/nchembio.221 1-deoxy-D-xylulose 5-phosphate reductoisomerase 3
23025997 10.1016/j.bmcl.2012.09.021 Unchecked 3
19783991 10.1038/nchembio.221 Outer membrane protein TolC 3
23795240 10.1021/ml300419r Unchecked 2
22024034 10.1016/j.bmcl.2011.09.123 Escherichia coli 2
22024034 10.1016/j.bmcl.2011.09.123 Staphylococcus aureus 2
21866890 10.1021/jm200694q Plasmodium berghei 2
23795240 10.1021/ml300419r Plasmodium falciparum 2
23819803 10.1021/jm4006498 Unchecked 2
22405649 10.1016/j.ejmech.2012.02.031 1-deoxy-D-xylulose 5-phosphate reductoisomerase 2
16439126 10.1016/j.bmcl.2005.12.082 Plasmodium falciparum 2
23819803 10.1021/jm4006498 1-deoxy-D-xylulose 5-phosphate reductoisomerase 2

Data from ChEMBL 36 via Core Engine