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Compound Detail

CHEMBL747

CYCLOGUANIL
🧪 Phase II
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🧪 Phase II
CC1(C)N=C(N)N=C(N)N1c1ccc(Cl)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL747
Name CYCLOGUANIL
Phase Phase II
Structure Type MOL
InChI Key QMNFFXRFOJIOKZ-UHFFFAOYSA-N

Known Names

Cycloguanil Malarone
16
Targets
87
Activities
4
Assay Types
0
PK Parameters
20
Publications
2
Known Names

Molecular Properties

251.7
MW (Da)
1.53
ALogP
5
HBA
2
HBD
80.0
PSA (Ų)
0.79
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 1964

Extended Properties

Molecular Formula C11H14ClN5
MW 251.72
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -0.61

Activity Summary

IC50 45 meas. best 9.93
Ki 33 meas. best 8.96
EC50 8 meas. best 7.42
Kd 1 meas. best 4.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 9.93 6.7648 0.1 29
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.96 7.24 1.1 16
Unchecked
CHEMBL612545
 Ki 8.82 7.2063 1.5 8
Enterococcus faecium
CHEMBL357
 IC50 7.77 7.77 17.0 1
Dihydrofolate reductase
CHEMBL1926
 Ki 7.63 7.295 23.3 2
Plasmodium falciparum
CHEMBL364
 EC50 7.42 7.42 38.0 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.4 5.622 40.0 5
Dihydrofolate reductase
CHEMBL202
 Ki 7.25 6.0033 55.6 3
Dihydrofolate reductase
CHEMBL2363
 IC50 6.96 6.96 110.0 1
Dihydrofolate reductase
CHEMBL2575
 Ki 6.95 6.95 112.2 1
Dihydrofolate reductase
CHEMBL1926
 IC50 6.35 6.35 450.0 1
Respiratory syncytial virus
CHEMBL612679
 EC50 6.26 6.26 550.0 1
Dihydrofolate reductase
CHEMBL1809
 Ki 5.99 5.99 1020.0 1
Unchecked
CHEMBL612545
 EC50 5.96 5.0933 1100.0 3
Influenza B virus
CHEMBL613129
 EC50 5.66 5.66 2200.0 1
Unchecked
CHEMBL612545
 IC50 5.3 5.3 5000.0 1
Dihydrofolate reductase
CHEMBL1809
 Kd 4.93 4.93 11770.0 1
Lacticaseibacillus casei
CHEMBL613075
 IC50 4.79 4.79 16300.0 1
Dihydrofolate reductase
CHEMBL2902
 Ki 4.76 4.76 17378.0 1
Dihydrofolate reductase
CHEMBL1809
 IC50 4.68 4.68 20910.0 1
Influenza A virus
CHEMBL613740
 EC50 4.54 4.51 29000.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.46 4.46 35000.0 1
KB
CHEMBL398
 IC50 4.39 4.39 41000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.118 nM 9.93 Antimalarial activity against Plasmodium falciparum D6 infected in RBCs assessed... 20566761
Plasmodium falciparum IC50 = 0.429 nM 9.37 Antimalarial activity against Plasmodium falciparum D6 harboring Plasmodium viva... 20566761
Plasmodium falciparum IC50 = 0.587 nM 9.23 Antimalarial activity against Plasmodium falciparum D6 harboring Plasmodium viva... 20566761
Plasmodium falciparum IC50 = 0.81 nM 9.09 Antimalarial activity against Plasmodium falciparum D6 harboring Plasmodium viva... 20566761
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.1 nM 8.96 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Unchecked Ki = 1.5 nM 8.82 Inhibition of Plasmodium falciparum DHFR expressed in Escherichia coli BL21 usin... 32294614
Unchecked Ki = 1.51 nM 8.82 Binding affinity to wild type Plasmodium falciparum DHFR by competitive binding ... 20350951
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.5 nM 8.82 Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falcipa... 14736247
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.5 nM 8.82 Evaluated for inhibition constant (Ki wt) against Wild-type dihydrofolate reduct... 10893311
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.6 nM 8.8 Inhibition constant against PfDHFR (Plasmodium falciparum dihydrofolate reductas... 12825927
Plasmodium falciparum IC50 = 1.699 nM 8.77 Antimalarial activity against Plasmodium falciparum D6 harboring Plasmodium viva... 20566761
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.6 nM 8.59 Inhibition constant against wild-type PfDHFR (Plasmodium falciparum dihydrofolat... 12825927
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.6 nM 8.59 Binding affinity was evaluated as inhibition of recombinant wild type (WT) Plasm... 9554869
Plasmodium falciparum IC50 = 2.77 nM 8.56 Antimalarial activity against Plasmodium falciparum D6 harboring Plasmodium viva... 20566761
Plasmodium falciparum IC50 = 7.5 nM 8.12 Antimalarial activity against Plasmodium falciparum 3D7 in erythrocytes 11844668
Plasmodium falciparum IC50 = 10.0 nM 8.0 Antiplasmodial activity against drug-sensitive blood stage Plasmodium falciparum... 29297684
Enterococcus faecium IC50 = 17.0 nM 7.77 Antibacterial activity against sensitive Streptococcus faecium ATCC 8043 assesse... 137981
Dihydrofolate reductase Ki = 23.3 nM 7.63 Binding affinity was reported with purified recombinant Pneumocystis carinii Dih... 7490723
Unchecked Ki = 31.4 nM 7.5 Inhibition of Plasmodium falciparum DHFR N51I/C59R/S108N mutant expressed in Esc... 32294614
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 31.4 nM 7.5 Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) o... 14736247

Literature References

PubMed DOI Target Context # Activities
14736247 10.1021/jm030165t Bifunctional dihydrofolate reductase-thymidylate synthase 15
20566761 10.1128/aac.00628-10 Plasmodium falciparum 14
7009867 10.1021/jm00134a002 Plasmodium berghei 7
7009867 10.1021/jm00134a002 Mus musculus 7
12825927 10.1021/jm030781p Bifunctional dihydrofolate reductase-thymidylate synthase 6
32294614 10.1016/j.ejmech.2020.112263 Plasmodium falciparum 6
32294614 10.1016/j.ejmech.2020.112263 Unchecked 6
10893311 10.1021/jm0009181 Bifunctional dihydrofolate reductase-thymidylate synthase 6
137981 10.1021/jm00212a010 Lacticaseibacillus casei 5
137981 10.1021/jm00212a010 Enterococcus faecium 5
28477572 10.1016/j.ejmech.2017.04.070 Unchecked 5
137981 10.1021/jm00212a010 NON-PROTEIN TARGET 4
26414808 10.1016/j.ejmech.2015.08.021 Dihydrofolate reductase 4
14736247 10.1021/jm030165t KB 4
30523084 10.1126/science.aat9446 Plasmodium berghei 4
20350951 10.1128/aac.01526-09 Unchecked 4
14736247 10.1021/jm030165t Vero 3
28477572 10.1016/j.ejmech.2017.04.070 Dihydrofolate reductase 3
14736247 10.1021/jm030165t BC 3
7490723 10.1021/jm00024a001 Dihydrofolate reductase 3

Data from ChEMBL 36 via Core Engine