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Compound Detail

CHEMBL258981

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CN(O)C(=O)CCCP(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL258981
Phase Preclinical
Structure Type MOL
InChI Key OXDGJHZVDJQJCC-UHFFFAOYSA-N
6
Targets
10
Activities
1
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

197.1
MW (Da)
-0.21
ALogP
3
HBA
3
HBD
98.1
PSA (Ų)
0.33
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 C5H12NO5P
MW 197.13
Aromatic Rings 0
Heavy Atoms 12
NP-Likeness 0.01

Activity Summary

IC50 10 meas. best 7.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL4091
 IC50 7.32 7.32 48.0 1
Unchecked
CHEMBL612545
 IC50 7.32 7.054 48.0 5
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL5630
 IC50 6.8 6.8 159.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL2010623
 IC50 6.39 6.39 410.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.01 6.01 980.0 1
1-deoxy-D-xylulose 5-phosphate reductoisomerase
CHEMBL3421521
 IC50 5.94 5.94 1150.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 48.0 nM 7.32 Inhibition of Escherichia coli recombinant His6-tagged DXR expressed in Escheric... 23025997
Unchecked IC50 = 48.0 nM 7.32 Inhibition of N-terminal His6-tagged Escherichia coli DXR after 2 mins in presen... 23414808
Unchecked IC50 = 48.0 nM 7.32 Inhibition of Escherichia coli His6-tagged DXR preincubated for 2 mins in presen... 27955925
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 48.0 nM 7.32 Inhibition of Escherichia coli DXR assessed as inhibition constant pre-incubated... 33303239
Unchecked IC50 = 97.0 nM 7.01 Inhibition of Escherichia coli DXR 18158249
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 159.0 nM 6.8 Inhibition of recombinant Mycobacterium tuberculosis Dxr expressed in Escherichi... 25781377
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 410.0 nM 6.39 Inhibition of Mycobacterium smegmatis DSM 43756 ATCC 19420 N-terminal his-tagged... 22405649
Unchecked IC50 = 500.0 nM 6.3 Inhibition of Escherichia coli recombinant His6-tagged DXR expressed in Escheric... 23025997
Plasmodium falciparum IC50 = 980.0 nM 6.01 Antimalarial activity against Plasmodium falciparum 3D7 in infected human erythr... 18158249
1-deoxy-D-xylulose 5-phosphate reductoisomerase IC50 = 1150.0 nM 5.94 Inhibition of recombinant Escherichia coli Dxr expressed in Escherichia coli BL2... 25781377

Literature References

PubMed DOI Target Context # Activities
23025997 10.1016/j.bmcl.2012.09.021 Unchecked 3
25781377 10.1021/jm5014264 Escherichia coli 3
25781377 10.1021/jm5014264 1-deoxy-D-xylulose 5-phosphate reductoisomerase 2
25781377 10.1021/jm5014264 Mycolicibacterium smegmatis 2
27955925 10.1016/j.bmc.2016.11.040 Escherichia coli 2
18158249 10.1016/j.bmc.2007.12.001 Unchecked 1
18158249 10.1016/j.bmc.2007.12.001 Plasmodium falciparum 1
22405649 10.1016/j.ejmech.2012.02.031 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1
22405649 10.1016/j.ejmech.2012.02.031 Mycolicibacterium smegmatis 1
23414808 10.1016/j.bmcl.2013.01.080 Unchecked 1
25781377 10.1021/jm5014264 Unchecked 1
25781377 10.1021/jm5014264 Plasmodium falciparum 1
27955925 10.1016/j.bmc.2016.11.040 Unchecked 1
27955925 10.1016/j.bmc.2016.11.040 Mycolicibacterium smegmatis 1
30344904 10.1021/acsmedchemlett.8b00223 Mycobacterium tuberculosis 1
33303239 10.1016/j.ejmech.2020.113055 1-deoxy-D-xylulose 5-phosphate reductoisomerase 1

Data from ChEMBL 36 via Core Engine