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Compound Detail

CHEMBL92583

CHLORCYCLOGUANIL
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CC1(C)N=C(N)N=C(N)N1c1ccc(Cl)c(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL92583
Name CHLORCYCLOGUANIL
Phase Preclinical
Structure Type MOL
InChI Key FPULLBVUFHTKQQ-UHFFFAOYSA-N
8
Targets
22
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

286.2
MW (Da)
2.18
ALogP
5
HBA
2
HBD
80.0
PSA (Ų)
0.83
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C11H13Cl2N5
MW 286.17
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.80

Activity Summary

IC50 10 meas. best 10.96
EC50 8 meas. best 8.12
Ki 4 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 10.96 7.7011 0.0 9
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.96 8.2667 1.1 3
Respiratory syncytial virus
CHEMBL612679
 EC50 8.12 8.12 7.5 1
Unchecked
CHEMBL612545
 EC50 7.52 6.5033 30.0 3
Influenza B virus
CHEMBL613129
 EC50 7.1 7.1 80.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 6.96 6.96 110.0 1
Influenza A virus
CHEMBL613740
 EC50 6.46 6.36 350.0 2
Mammalian orthoreovirus 1
CHEMBL612927
 EC50 5.42 5.42 3800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.011 nM 10.96 Antimalarial activity against pyrimethamine-sensitive Plasmodium falciparum 3D7 ... 19528269
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.1 nM 8.96 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.1 nM 8.96 Evaluated for inhibition constant (Ki wt) against Wild-type dihydrofolate reduct... 10893311
Plasmodium falciparum IC50 = 4.0 nM 8.4 Growth inhibition (IC50) against Plasmodium falciparum wild-type TM4/8.2 10893311
Respiratory syncytial virus EC50 = 7.5 nM 8.12 Antiviral activity against Respiratory syncytial virus infected in human HeLa ce... 28477572
Unchecked EC50 = 30.0 nM 7.52 Antiviral activity against Influenza B virus B/Ned/537/05 infected in MDCK cells... 28477572
Plasmodium falciparum IC50 = 37.8 nM 7.42 Antimalarial activity against Plasmodium falciparum Kenyan isolates by [3H]hypox... 19528269
Plasmodium falciparum IC50 = 38.06 nM 7.42 Antimalarial activity against Plasmodium falciparum Kenyan isolates expressing D... 19528269
Plasmodium falciparum IC50 = 39.99 nM 7.4 Antimalarial activity against Plasmodium falciparum Kenyan isolates expressing D... 19528269
Plasmodium falciparum IC50 = 79.0 nM 7.1 Antiplasmodial activity against multidrug-resistant Plasmodium falciparum VS/1 b... 19364853
Influenza B virus EC50 = 80.0 nM 7.1 Antiviral activity against Influenza B virus B/Ned/537/05 infected in MDCK cells... 28477572
Plasmodium falciparum IC50 = 87.68 nM 7.06 Antimalarial activity against Plasmodium falciparum isolate Kil-164 expressing D... 19528269
Plasmodium falciparum IC50 = 92.3 nM 7.04 Antimalarial activity against pyrimethamine-resistant Plasmodium falciparum V1S ... 19528269
Dihydrofolate reductase Ki = 110.0 nM 6.96 Inhibition of human DHFR using dihydrofolate as substrate after 180 secs by spec... 28477572
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 130.7 nM 6.88 Inhibition constant (Ki mut) against A16V+S108T Mutant DHFRs of Plasmodium falci... 10893311
Plasmodium falciparum IC50 = 307.0 nM 6.51 Growth inhibition IC50 against Plasmodium falciparum mutant T9/94 10893311
Influenza A virus EC50 = 350.0 nM 6.46 Antiviral activity against Influenza A virus A/Ned/378/05(H1N1) infected in MDCK... 28477572
Influenza A virus EC50 = 550.0 nM 6.26 Antiviral activity against Influenza A virus A/Ned/378/05(H1N1) infected in MDCK... 28477572
Unchecked EC50 = 720.0 nM 6.14 Antiviral activity against Influenza A virus A/Virginia/ATCC3/2009(H1N1) infecte... 28477572
Unchecked EC50 = 1400.0 nM 5.85 Antiviral activity against Influenza A virus A/Virginia/ATCC3/2009(H1N1) infecte... 28477572

Literature References

PubMed DOI Target Context # Activities
10893311 10.1021/jm0009181 Bifunctional dihydrofolate reductase-thymidylate synthase 6
19528269 10.1128/aac.00308-09 Plasmodium falciparum 6
28477572 10.1016/j.ejmech.2017.04.070 Unchecked 5
10893311 10.1021/jm0009181 Plasmodium falciparum 2
28477572 10.1016/j.ejmech.2017.04.070 Influenza A virus 2
28477572 10.1016/j.ejmech.2017.04.070 MDCK 2
28477572 10.1016/j.ejmech.2017.04.070 Coxsackievirus B4 2
28477572 10.1016/j.ejmech.2017.04.070 Influenza B virus 1
28477572 10.1016/j.ejmech.2017.04.070 Dihydrofolate reductase 1
28477572 10.1016/j.ejmech.2017.04.070 Yellow fever virus 1
28477572 10.1016/j.ejmech.2017.04.070 Punta Toro virus 1
28477572 10.1016/j.ejmech.2017.04.070 Sindbis virus 1
28477572 10.1016/j.ejmech.2017.04.070 Mammalian orthoreovirus 1 1
28477572 10.1016/j.ejmech.2017.04.070 Human respirovirus 3 1
28477572 10.1016/j.ejmech.2017.04.070 HeLa 1
28477572 10.1016/j.ejmech.2017.04.070 Vesicular stomatitis virus 1
1895302 10.1021/jm00113a022 Dihydrofolate reductase 1
19364853 10.1128/aac.01689-08 Plasmodium falciparum 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
15293997 10.1021/jm040769c Bifunctional dihydrofolate reductase-thymidylate synthase 1

Data from ChEMBL 36 via Core Engine