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Compound Detail

CHEMBL267616

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COc1ccc(CC2CCc3nc(N)nc(N)c3C2)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267616
Phase Preclinical
Structure Type MOL
InChI Key XVXBYTNVUPDKPO-UHFFFAOYSA-N
26
Targets
27
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

314.4
MW (Da)
2.01
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.90
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H22N4O2
MW 314.39
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.14

Activity Summary

IC50 27 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL2425
 IC50 7.64 7.64 23.0 1
HCT-116
CHEMBL394
 IC50 7.4 7.4 40.0 1
NCI-H460
CHEMBL396
 IC50 7.4 7.4 40.0 1
MDA-N
CHEMBL614078
 IC50 7.29 7.29 51.0 1
A549
CHEMBL392
 IC50 7.22 7.22 60.0 1
786-0
CHEMBL613102
 IC50 7.22 7.22 60.0 1
Dihydrofolate reductase
CHEMBL2363
 IC50 7.2 7.2 63.0 1
LOX IMVI
CHEMBL614096
 IC50 7.16 7.16 70.0 1
PC-3
CHEMBL390
 IC50 7.14 7.14 72.0 1
Unchecked
CHEMBL612545
 IC50 7.09 7.09 81.0 1
Dihydrofolate reductase
CHEMBL1926
 IC50 7.0 7.0 100.0 1
IGROV-1
CHEMBL613984
 IC50 6.89 6.89 130.0 1
ACHN
CHEMBL614519
 IC50 6.62 6.62 240.0 1
SF-295
CHEMBL614908
 IC50 6.6 6.6 250.0 1
BT-549
CHEMBL614072
 IC50 6.57 6.57 270.0 1
SF-268
CHEMBL613977
 IC50 6.52 6.52 300.0 1
SW-620
CHEMBL612262
 IC50 6.0 6.0 990.0 1
KM12
CHEMBL614709
 IC50 5.89 5.89 1300.0 1
COLO 205
CHEMBL614561
 IC50 5.42 5.42 3800.0 1
EKVX
CHEMBL614487
 IC50 5.24 5.24 5700.0 1
NCI-H226
CHEMBL614740
 IC50 4.92 4.92 12000.0 1
UACC-257
CHEMBL612796
 IC50 4.82 4.82 15000.0 1
T47D
CHEMBL614361
 IC50 4.72 4.72 19000.0 1
OVCAR-8
CHEMBL612555
 IC50 4.68 4.68 21000.0 1
SN12C
CHEMBL614054
 IC50 4.64 4.64 23000.0 1
A498
CHEMBL614516
 IC50 4.62 4.62 24000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 23.0 nM 7.64 The ability to inhibit Toxoplasma gondii Dihydrofolate reductase was tested 10090784
NCI-H460 IC50 = 40.0 nM 7.4 Compound was tested for the growth inhibition of NCI-H460 lung tumor cell line 10090784
HCT-116 IC50 = 40.0 nM 7.4 Compound was tested for the growth inhibition of HCT116 colon tumor cell line 10090784
MDA-N IC50 = 51.0 nM 7.29 Compound was tested for the growth inhibition of MDA-N breast carcinoma cell lin... 10090784
A549 IC50 = 60.0 nM 7.22 Compound was tested for the growth inhibition of A549 lung tumor cell line 10090784
786-0 IC50 = 60.0 nM 7.22 Compound was tested for the growth inhibition of 786-0 renal tumor cell line 10090784
Dihydrofolate reductase IC50 = 63.0 nM 7.2 The ability to inhibit rat liver Dihydrofolate reductase was tested 10090784
LOX IMVI IC50 = 70.0 nM 7.16 Compound was tested for the growth inhibition of LOX IMVI melanoma tumor cell li... 10090784
PC-3 IC50 = 72.0 nM 7.14 Compound was tested for the growth inhibition of PC3 prostate tumor cell line 10090784
Unchecked IC50 = 81.0 nM 7.09 The ability to inhibit [3H]- uracil incorporation by Toxoplasma gondii in cultur... 10090784
Dihydrofolate reductase IC50 = 100.0 nM 7.0 The ability to inhibit Pneumocystis carinii Dihydrofolate reductase was tested 10090784
IGROV-1 IC50 = 130.0 nM 6.89 Compound was tested for the growth inhibition of IGROV1 ovarian tumor cell line 10090784
ACHN IC50 = 240.0 nM 6.62 Compound was tested for the growth inhibition of ACHN renal tumor cell line 10090784
SF-295 IC50 = 250.0 nM 6.6 Compound was tested for the growth inhibition of SF-295 CNS tumor cell line 10090784
BT-549 IC50 = 270.0 nM 6.57 Compound was tested for the growth inhibition of BT-549 breast carcinoma cell li... 10090784
SF-268 IC50 = 300.0 nM 6.52 Compound was tested for the growth inhibition of SF-268 CNS tumor cell line 10090784
SW-620 IC50 = 990.0 nM 6.0 Compound was tested for the growth inhibition of SW-620 colon tumor cell line 10090784
KM12 IC50 = 1300.0 nM 5.89 Compound was tested for the growth inhibition of KM12 colon tumor cell line 10090784
COLO 205 IC50 = 3800.0 nM 5.42 Compound was tested for the growth inhibition of COLO 205 colon tumor cell line 10090784
EKVX IC50 = 5700.0 nM 5.24 Compound was tested for the growth inhibition of EKVX lung tumor cell line 10090784

Literature References

PubMed DOI Target Context # Activities
10090784 10.1021/jm980572i Unchecked 2
10090784 10.1021/jm980572i Dihydrofolate reductase 2
10090784 10.1021/jm980572i SW-620 1
20185316 10.1016/j.bmc.2010.01.068 Cryptosporidium parvum 1
10090784 10.1021/jm980572i IGROV-1 1
10090784 10.1021/jm980572i UACC-257 1
10090784 10.1021/jm980572i SK-MEL-5 1
10090784 10.1021/jm980572i LOX IMVI 1
10090784 10.1021/jm980572i SF-539 1
10090784 10.1021/jm980572i SF-295 1
10090784 10.1021/jm980572i SF-268 1
10090784 10.1021/jm980572i COLO 205 1
10090784 10.1021/jm980572i KM12 1
10090784 10.1021/jm980572i HCT-116 1
10090784 10.1021/jm980572i NCI-H226 1
10090784 10.1021/jm980572i EKVX 1
10090784 10.1021/jm980572i A549 1
10090784 10.1021/jm980572i NCI-H460 1
10090784 10.1021/jm980572i Dihydrofolate reductase; T. gondii vs rat 1
10090784 10.1021/jm980572i Dihydrofolate reductase; P. carinii vs rat 1

Data from ChEMBL 36 via Core Engine