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Compound Detail

CHEMBL935

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N=C(N)c1ccc(OCCCCCOc2ccc(C(=N)N)cc2)cc1.O=S(=O)(O)CCO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL935
Phase Preclinical
Structure Type MOL
InChI Key NYRHYBFMOOPIRI-UHFFFAOYSA-N
Parent Compound CHEMBL55
Active Moiety CHEMBL55
13
Targets
44
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

340.4
MW (Da)
2.88
ALogP
4
HBA
4
HBD
118.2
PSA (Ų)
0.30
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H30N4O6S
MW 466.56
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.14

Activity Summary

IC50 33 meas. best 10.05
EC50 11 meas. best 8.98

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 10.05 8.042 0.1 15
Trypanosoma brucei brucei
CHEMBL612851
 IC50 9.07 9.07 0.9 1
Trypanosoma brucei brucei
CHEMBL612851
 EC50 8.98 8.96 1.1 2
Trypanosoma brucei rhodesiense
CHEMBL612348
 EC50 8.43 8.43 3.7 1
Unchecked
CHEMBL612545
 EC50 7.26 5.1629 55.0 7
Leishmania amazonensis
CHEMBL612877
 IC50 6.34 6.34 460.0 1
Leishmania tropica
CHEMBL612881
 IC50 6.21 6.21 620.0 1
Leishmania donovani
CHEMBL367
 IC50 6.06 5.6033 880.0 3
Leishmania major
CHEMBL612879
 IC50 6.02 5.05 960.0 2
Unchecked
CHEMBL612545
 IC50 5.82 4.8125 1506.0 4
Leishmania infantum
CHEMBL612848
 IC50 5.82 5.82 1500.0 2
Rattus norvegicus
CHEMBL376
 IC50 5.6 5.6 2500.0 1
KB
CHEMBL398
 IC50 5.57 5.57 2700.0 1
Leishmania braziliensis
CHEMBL612878
 IC50 4.71 4.71 19600.0 1
Streptokinase A
CHEMBL1293228
 EC50 4.55 4.55 27910.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.09 nM 10.05 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.19 nM 9.72 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.23 nM 9.64 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 0.25 nM 9.6 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.26 nM 9.59 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.28 nM 9.55 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Trypanosoma brucei brucei IC50 = 0.86 nM 9.07 Antitrypanosomal activity against blood stream form of Trypanosoma brucei brucei... 21757346
Plasmodium falciparum IC50 = 1.0 nM 9.0 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Trypanosoma brucei brucei EC50 = 1.05 nM 8.98 Antitrypanosomal activity against Trypanosoma brucei brucei BF427 assessed as gr... 27992217
Trypanosoma brucei brucei EC50 = 1.15 nM 8.94 Antitrypanosomal activity against Trypanosoma brucei brucei BF427 measured after... 28835807
Trypanosoma brucei rhodesiense EC50 = 3.7 nM 8.43 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei rhodesi... 22119463
Plasmodium falciparum IC50 = 42.0 nM 7.38 Antiplasmodial activity against Plasmodium falciparum 3D7 infected in RBCs by fi... 20547797
Unchecked EC50 = 55.0 nM 7.26 PubChem BioAssay. Leishmania major promastigote EC50 determinations. (Class of... -
Plasmodium falciparum IC50 = 100.0 nM 7.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 199.53 nM 6.7 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 251.19 nM 6.6 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 251.19 nM 6.6 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 251.19 nM 6.6 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 251.19 nM 6.6 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Leishmania amazonensis IC50 = 460.0 nM 6.34 Tested for growth inhibitory activity against Leishmania amazonensis promastigot... 15481980

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 14
20660673 10.1128/aac.01065-09 Staphylococcus aureus 10
25835356 10.1016/j.bmc.2015.03.029 Trypanosoma brucei brucei 7
27992217 10.1021/acs.jmedchem.6b01163 Unchecked 4
32392053 10.1021/acs.jmedchem.9b02016 Unchecked 4
27992217 10.1021/acs.jmedchem.6b01163 Trypanosoma brucei brucei 2
27992217 10.1021/acs.jmedchem.6b01163 HepG2 2
26076227 10.1021/np5008697 Unchecked 2
15481980 10.1021/jm0401006 No relevant target 2
15481980 10.1021/jm0401006 Leishmania amazonensis 2
17417631 10.1038/nchembio873 Unchecked 1
20547797 10.1128/aac.00431-10 Plasmodium falciparum 1
19743860 10.1021/jm900564x Unchecked 1
21757346 10.1016/j.bmcl.2011.06.059 Trypanosoma brucei brucei 1
22119463 10.1016/j.bmcl.2011.10.108 Trypanosoma brucei rhodesiense 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
32283298 10.1016/j.ejmech.2020.112275 Plasmodium 1
19743860 10.1021/jm900564x KB 1
19743860 10.1021/jm900564x Leishmania donovani 1
26076227 10.1021/np5008697 Leishmania donovani 1

Data from ChEMBL 36 via Core Engine