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Compound Detail

CHEMBL381751

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CN(C/C=C\CN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL381751
Phase Preclinical
Structure Type MOL
InChI Key YWJCZGDVJQLZET-GGHFOJMISA-N
6
Targets
18
Activities
2
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

349.4
MW (Da)
-1.53
ALogP
10
HBA
4
HBD
148.6
PSA (Ų)
0.46
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H23N7O3
MW 349.40
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 0.62

Activity Summary

IC50 12 meas. best 8.85
EC50 6 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 8.85 7.574 1.4 5
Trypanosoma brucei
CHEMBL612849
 EC50 8.0 8.0 10.0 1
Trypanosoma brucei brucei
CHEMBL612851
 EC50 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
 IC50 7.39 6.8 41.0 3
Trypanosoma brucei brucei
CHEMBL612851
 IC50 7.0 6.84 100.0 2
A549
CHEMBL392
 IC50 5.52 5.52 3000.0 1
Leishmania donovani
CHEMBL367
 EC50 4.4 4.4 40000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 20690.0 ng.hr.mL-1 Mus musculus
AUC 360.0 ng.hr.mL-1 Mus musculus
AUC 20690.0 ng.hr.mL-1 Mus musculus
AUC 360.0 ng.hr.mL-1 Mus musculus
CL 11.0 mL.min-1.kg-1 Rattus norvegicus
CL 11.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.2 mL.min-1.kg-1 Homo sapiens
CL 4.2 mL.min-1.kg-1 Homo sapiens
Cmax 128219.81 nM Mus musculus
Cmax 228.96 nM Mus musculus
Cmax 128219.81 nM Mus musculus
Cmax 228.96 nM Mus musculus
T1/2 2.48 hr Mus musculus
T1/2 2.48 hr Mus musculus
T1/2 1.5 hr Homo sapiens
T1/2 1.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei rhodesiense IC50 = 1.4 nM 8.85 Antiparasitic activity against Trypanosoma brucei rhodesiense STIB 900 clone aft... 19289530
Trypanosoma brucei brucei EC50 = 10.0 nM 8.0 Antitrypanosomal activity against Trypanosoma brucei brucei 28807574
Trypanosoma brucei EC50 = 10.0 nM 8.0 Antitrypanosomal activity against Trypanosoma brucei Lister 427 bloodstream form... 28807574
Trypanosoma brucei rhodesiense IC50 = 11.0 nM 7.96 Antitrypanosomal activity against Trypanosoma brucei rhodesiense 19419862
Trypanosoma brucei rhodesiense IC50 = 40.0 nM 7.4 In vitro antitrypanosomal activity against Trypanosomal 243 (KETRI)strain 12408722
Unchecked IC50 = 41.0 nM 7.39 Inhibition of His-tagged Trypanosoma brucei AdoMetDC expressed in Escherichia co... 28807574
Unchecked IC50 = 41.0 nM 7.39 Inhibition of Trypanosoma brucei AdoMetDC pre-incubated for 30 mins before AdoMe... 28807574
Trypanosoma brucei brucei IC50 = 100.0 nM 7.0 In vitro antitrypanosomal activity against Trypanosomal 110 (EATRO)strain 12408722
Trypanosoma brucei rhodesiense IC50 = 100.0 nM 7.0 In vitro antitrypanosomal activity against Trypanosomal 243 As 10e-3 (KETRI)stra... 12408722
Trypanosoma brucei brucei IC50 = 210.0 nM 6.68 Antitrypanosomal activity against Trypanosoma brucei brucei 19419862
Trypanosoma brucei rhodesiense IC50 = 220.0 nM 6.66 In vitro antitrypanosomal activity against Trypanosomal 269 (KETRI)strain 12408722
Unchecked IC50 = 2400.0 nM 5.62 Inhibition of Trypanosoma brucei AdoMetDC without pre-incubation for 30 mins bef... 28807574
A549 IC50 = 3000.0 nM 5.52 In vitro Antineoplastic Activity against Human non small cell lung carcinoma A54... 12408722
Leishmania donovani EC50 = 40000.0 nM 4.4 Antiproliferative activity against Leishmania donovani DI700 promastigotes 17116678

Literature References

PubMed DOI Target Context # Activities
12408722 10.1021/jm0201621 Trypanosoma brucei rhodesiense 6
12408722 10.1021/jm0201621 Mus musculus 6
17116678 10.1128/aac.01193-06 Leishmania donovani 6
19289530 10.1128/aac.01674-08 Plasma 4
12408722 10.1021/jm0201621 Trypanosoma brucei brucei 4
19289530 10.1128/aac.01674-08 ADMET 4
19289530 10.1128/aac.01674-08 Trypanosoma brucei brucei 4
28807574 10.1016/j.bmc.2017.07.063 Unchecked 3
12408722 10.1021/jm0201621 MCF7 2
19289530 10.1128/aac.01674-08 S-adenosylmethionine decarboxylase proenzyme 2
19289530 10.1128/aac.01674-08 Caco-2 2
19289530 10.1128/aac.01674-08 Liver microsomes 2
19289530 10.1128/aac.01674-08 Hepatocyte 2
19451291 10.1128/aac.00076-09 Trypanosoma brucei rhodesiense 2
19419862 10.1016/j.bmcl.2009.04.096 Trypanosoma brucei brucei 2
19419862 10.1016/j.bmcl.2009.04.096 Blood 2
19289530 10.1128/aac.01674-08 Brain 2
19419862 10.1016/j.bmcl.2009.04.096 Brain 2
28807574 10.1016/j.bmc.2017.07.063 Liver 2
19289530 10.1128/aac.01674-08 Blood 2

Data from ChEMBL 36 via Core Engine