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Compound Detail

CHEMBL2164257

FOSMIDOMYCIN SODIUM
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O=CN(O)CCCP(=O)([O-])O.[Na+]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2164257
Name FOSMIDOMYCIN SODIUM
Phase Preclinical
Structure Type MOL
InChI Key ZZPUYRHMTGOTEU-UHFFFAOYSA-M
Parent Compound CHEMBL203125
Active Moiety CHEMBL203125
6
Targets
21
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

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
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C4H9NNaO5P
MW 205.08
Aromatic Rings 0
Heavy Atoms 11
NP-Likeness 0.55

Activity Summary

IC50 20 meas. best 8.1
Ki 1 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL4091
 IC50 8.1 7.3567 8.0 3
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic
CHEMBL4295619
 Ki 7.7 7.7 20.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic
CHEMBL4295619
 IC50 7.47 7.1533 34.0 3
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL5630
 IC50 7.1 6.87 80.0 2
Plasmodium falciparum
CHEMBL364
 IC50 7.05 6.095 90.0 10
Unchecked
CHEMBL612545
 IC50 6.8 6.8 160.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL3421521
 IC50 6.66 6.66 220.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 30.0 % Homo sapiens
F 20.0 % Homo sapiens
F 20.0 % Homo sapiens
T1/2 2.0 hr Homo sapiens
T1/2 1.87 hr Homo sapiens
T1/2 1.87 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 8.0 nM 8.1 Inhibition of recombinant Escherichia coli DXR in presence of NADPH by microplat... 33303239
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic Ki = 20.0 nM 7.7 Inhibition of Plasmodium falciparum DXR assessed as inhibition constant incubate... 36399924
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic IC50 = 34.0 nM 7.47 Inhibition of Plasmodium falciparum DXR 30192536
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 49.0 nM 7.31 Inhibition of His-tagged Escherichia coli DXR using DXP as substrate incubated f... 33303239
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic IC50 = 64.0 nM 7.19 Inhibition of Plasmodium falciparum DXR assessed as reduction in NADPH oxidation... 30192536
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 80.0 nM 7.1 Inhibition of Mycobacterium tuberculosis DXR in presence of NADPH by spectrophot... 33303239
Plasmodium falciparum IC50 = 90.0 nM 7.05 Growth inhibition of Plasmodium falciparum 30192536
Unchecked IC50 = 160.0 nM 6.8 Inhibition of recombinant Plasmodium falciparum recombinant IspC using [3,4,5-13... 22731758
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic IC50 = 160.0 nM 6.8 Inhibition of recombinant Plasmodium falciparum IspC expressed in Escherichia co... 31382119
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 220.0 nM 6.66 Inhibition of Escherichia coli M15 recombinant IspC using 1-deoxy-D-xylulose 5-p... 25254502
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 220.0 nM 6.66 Inhibition of recombinant Escherichia coli IspC expressed in Escherichia coli M1... 31382119
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 230.0 nM 6.64 Inhibition of recombinant Mycobacterium tuberculosis IspC expressed in Escherich... 31382119
Plasmodium falciparum IC50 = 810.0 nM 6.09 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Dd2 ... 22731758
Plasmodium falciparum IC50 = 810.0 nM 6.09 Antimalarial activity against asexual blood stages of Plasmodium falciparum Dd2 ... 31382119
Plasmodium falciparum IC50 = 880.0 nM 6.06 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 22731758
Plasmodium falciparum IC50 = 880.0 nM 6.06 Antimalarial activity against asexual blood stages of Plasmodium falciparum 3D7 ... 31382119
Plasmodium falciparum IC50 = 1087.0 nM 5.96 Growth inhibition of Plasmodium falciparum 3D7 asynchronous cultures by PicoGree... 30192536
Plasmodium falciparum IC50 = 1100.0 nM 5.96 Antiplasmodial activity against asexual blood stage chloroquine-resistant Plasmo... 36399924
Plasmodium falciparum IC50 = 1100.0 nM 5.96 Antiplasmodial activity against asexual blood stage pyrimethamine-resistant Plas... 36399924
Plasmodium falciparum IC50 = 1100.0 nM 5.96 Antiplasmodial activity against asexual blood stage mefloquine-resistant Plasmod... 36399924

Literature References

PubMed DOI Target Context # Activities
36399924 10.1016/j.ejmech.2022.114924 Plasmodium falciparum 3
33303239 10.1016/j.ejmech.2020.113055 1-deoxy-D-xylulose 5-phosphate reductoisomerase 3
30192536 10.1021/acs.jmedchem.8b01026 1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic 3
30192536 10.1021/acs.jmedchem.8b01026 Plasmodium falciparum 2
30344904 10.1021/acsmedchemlett.8b00223 Homo sapiens 2
30857749 10.1016/j.bmcl.2019.03.008 ADMET 2
30879839 10.1016/j.bmcl.2019.03.009 ADMET 2
22731758 10.1021/jm300652f Plasmodium falciparum 2
31382119 10.1016/j.ejmech.2019.07.058 Plasmodium falciparum 2
31382119 10.1016/j.ejmech.2019.07.058 1-deoxy-D-xylulose 5-phosphate reductoisomerase 2
30879839 10.1016/j.bmcl.2019.03.009 Plasmodium falciparum 1
36399924 10.1016/j.ejmech.2022.114924 ADMET 1
31790578 10.1021/acs.jmedchem.9b01483 Mitochondrial amidoxime reducing component 2 1
31382119 10.1016/j.ejmech.2019.07.058 HeLa 1
31382119 10.1016/j.ejmech.2019.07.058 1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic 1
30879839 10.1016/j.bmcl.2019.03.009 MRC5 1
30879839 10.1016/j.bmcl.2019.03.009 Mycobacterium tuberculosis 1
30344904 10.1021/acsmedchemlett.8b00223 Mycobacterium tuberculosis 1
30344904 10.1021/acsmedchemlett.8b00223 MRC5 1
25254502 10.1021/jm500850y 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1

Data from ChEMBL 36 via Core Engine