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Compound Detail

CHEMBL371502

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Nc1ncnc2c1ncn2[C@@H]1O[C@H](COS(=O)(=O)NC(=O)c2ccccc2O)[C@@H](O)[C@H]1O

Basic Information

ChEMBL ID CHEMBL371502
Phase Preclinical
Structure Type MOL
InChI Key SABYITLYKSVAAD-CNEMSGBDSA-N
8
Targets
13
Activities
2
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

466.4
MW (Da)
-1.58
ALogP
13
HBA
5
HBD
212.0
PSA (Ų)
0.28
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H18N6O8S
MW 466.43
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness 0.46

Activity Summary

IC50 9 meas. best 8.15
Ki 4 meas. best 8.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
AMP-binding enzyme family protein
CHEMBL3308969
Ki 8.97 8.97 1.1 1
Enoyl-[acyl-carrier-protein] reductase [NADH]
CHEMBL1849
Ki 8.18 8.18 6.6 1
Salicyl-AMP ligase / salicyl-S-ArCP synthetase
CHEMBL5662
Ki 8.18 8.18 6.6 1
AMP-binding enzyme family protein
CHEMBL3308969
IC50 8.15 7.7667 7.0 3
Salicyl-AMP ligase / salicyl-S-ArCP synthetase
CHEMBL5662
IC50 7.97 7.97 10.7 1
Pyochelin synthase PchD
CHEMBL3308937
IC50 7.9 7.9 12.5 1
Anthranilate--CoA ligase
CHEMBL4295626
Ki 7.06 7.06 88.0 1
Mycobacterium tuberculosis
CHEMBL360
IC50 5.66 5.03 2200.0 2
Yersinia pestis
CHEMBL614597
IC50 4.29 4.29 51200.0 1
Transient receptor potential cation channel subfamily M member 2
CHEMBL1250402
IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8650.0 ng.hr.mL-1 Rattus norvegicus
AUC 1100.0 ng.hr.mL-1 Rattus norvegicus
CL 4.9 mL.min-1.kg-1 Rattus norvegicus
F 1.0 % Rattus norvegicus
T1/2 0.1833 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
AMP-binding enzyme family protein Ki = 1.08 nM 8.97 Competitive inhibition of Yersinia pestis YbtE in presence of increasing concent... 16407990
Salicyl-AMP ligase / salicyl-S-ArCP synthetase Ki = 6.6 nM 8.18 Inhibition of Mycobacterium tuberculosis MbtA expressed in Escherichia coli asse... 19053762
Enoyl-[acyl-carrier-protein] reductase [NADH] Ki = 6.6 nM 8.18 Binding affinity to Mycobacterium tuberculosis InhA 37859726
AMP-binding enzyme family protein IC50 = 7.0 nM 8.15 Inhibition of Yersinia pestis YbtE assessed as incorporation of [3H]salicyl grou... 18394884
Salicyl-AMP ligase / salicyl-S-ArCP synthetase IC50 = 10.7 nM 7.97 Inhibition of adenylation activity of Mycobacterium tuberculosis MbtA after 30 m... 16407990
Pyochelin synthase PchD IC50 = 12.5 nM 7.9 Inhibition of adenylation activity of Pseudomonas aeruginosa PchD after 15 mins ... 16407990
AMP-binding enzyme family protein IC50 = 14.7 nM 7.83 Inhibition of adenylation activity of Yersinia pestis YbtE after 15 mins by ATP-... 16407990
AMP-binding enzyme family protein IC50 = 47.9 nM 7.32 Inhibition of His6-tagged Yersinia pestis YbtE-mediated [3H]salicyl-ypArCP-H6 fo... 16407990
Anthranilate--CoA ligase Ki = 88.0 nM 7.06 Inhibition of recombinant Pseudomonas aeruginosa PqsA assessed as decrease in fo... 29999316
Mycobacterium tuberculosis IC50 = 2200.0 nM 5.66 Antimicrobial activity against Mycobacterium tuberculosis H37Rv assessed as inhi... 16407990
Mycobacterium tuberculosis IC50 = 39900.0 nM 4.4 Antimicrobial activity against Mycobacterium tuberculosis H37Rv assessed as inhi... 16407990
Yersinia pestis IC50 = 51200.0 nM 4.29 Antimicrobial activity against Yersinia pestis assessed as inhibition of bacteri... 16407990
Transient receptor potential cation channel subfamily M member 2 IC50 = 100000.0 nM 4.0 Antagonist activity at human TRPM2 expressed in HEK293 cells assessed as inhibit... 24304219

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3832761 Mycobacterium tuberculosis 17
29670706 10.1021/acsmedchemlett.8b00090 Rattus norvegicus 6
37859726 10.1039/d3md00201b Mycobacterium tuberculosis 4
16407990 10.1038/nchembio706 Mycobacterium tuberculosis 4
17967002 10.1021/jm070905o Mycobacterium tuberculosis 3
29670706 10.1021/acsmedchemlett.8b00090 Mycobacterium tuberculosis 3
24304219 10.1021/jm401497a Transient receptor potential cation channel subfamily M member 2 3
16407990 10.1038/nchembio706 Yersinia pestis 3
16407990 10.1038/nchembio706 AMP-binding enzyme family protein 3
16392788 10.1021/jm051060o Mycobacterium tuberculosis 2
19053762 10.1021/jm8008037 Mycobacterium tuberculosis 2
16407990 10.1038/nchembio706 Pyochelin synthase PchD 1
16407990 10.1038/nchembio706 Salicyl-AMP ligase / salicyl-S-ArCP synthetase 1
19053762 10.1021/jm8008037 Vero 1
19053762 10.1021/jm8008037 ADMET 1
26875934 10.1016/j.bmc.2016.02.002 No relevant target 1
- 10.6019/CHEMBL3832761 HepG2 1
37859726 10.1039/d3md00201b Enoyl-[acyl-carrier-protein] reductase [NADH] 1
19053762 10.1021/jm8008037 Salicyl-AMP ligase / salicyl-S-ArCP synthetase 1
18394884 10.1016/j.bmcl.2008.03.025 AMP-binding enzyme family protein 1

Data from ChEMBL 36 via Core Engine