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Compound Detail

CHEMBL36739

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Nc1nc(=O)c2cc(NCc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)ccc2[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL36739
Phase Preclinical
Structure Type MOL
InChI Key MXBUWHDMZGKTHK-UHFFFAOYSA-N
8
Targets
17
Activities
1
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

439.4
MW (Da)
1.17
ALogP
7
HBA
6
HBD
187.5
PSA (Ų)
0.28
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H21N5O6
MW 439.43
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.50

Activity Summary

IC50 17 meas. best 6.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL202
 IC50 6.96 6.96 110.0 2
HT-29
CHEMBL384
 IC50 6.22 5.92 600.0 3
WiDr
CHEMBL614647
 IC50 6.22 5.66 600.0 3
Unchecked
CHEMBL612545
 IC50 6.16 5.755 700.0 2
SW480
CHEMBL612544
 IC50 5.96 5.5533 1100.0 3
Thymidylate synthase
CHEMBL3160
 IC50 5.89 5.89 1300.0 2
L1210
CHEMBL386
 IC50 5.5 5.5 3200.0 1
HuTu80
CHEMBL614582
 IC50 5.35 5.35 4500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase IC50 = 110.0 nM 6.96 Inhibition of human WIL2/dihydrofolate reductase activity 2704031
Dihydrofolate reductase IC50 = 110.0 nM 6.96 Inhibitory activity against dihydrofolate reductase (DHFR) obtained from human W... 3339615
HT-29 IC50 = 600.0 nM 6.22 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
WiDr IC50 = 600.0 nM 6.22 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
Unchecked IC50 = 700.0 nM 6.16 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
SW480 IC50 = 1100.0 nM 5.96 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
Thymidylate synthase IC50 = 1300.0 nM 5.89 Inhibitory activity against thymidylate synthase isolated from L1210 leukemia ce... 3339615
Thymidylate synthase IC50 = 1300.0 nM 5.89 Inhibition of L1210 leukemia thymidylate synthase (TS) enzyme 2704031
HT-29 IC50 = 1700.0 nM 5.77 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
HT-29 IC50 = 1700.0 nM 5.77 Inhibition of cell growth against HT-29 human gastrointestinal adenocarcinoma ce... 3612694
L1210 IC50 = 3200.0 nM 5.5 Inhibition of the growth of methotrexate sensitive L1210 leukemia/S cells in cul... 2704031
WiDr IC50 = 4200.0 nM 5.38 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
WiDr IC50 = 4200.0 nM 5.38 Inhibition of cell growth against WIDR human gastrointestinal adenocarcinoma cel... 3612694
Unchecked IC50 = 4500.0 nM 5.35 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
SW480 IC50 = 4500.0 nM 5.35 In vitro inhibition of growth of the human gastrointestinal adenocarcinoma cells... 6694171
HuTu80 IC50 = 4500.0 nM 5.35 Inhibition of cell growth against HuTu 80 human gastrointestinal adenocarcinoma ... 3612694
SW480 IC50 = 4500.0 nM 5.35 Inhibition of cell growth against SW480 human gastrointestinal adenocarcinoma ce... 3612694

Literature References

PubMed DOI Target Context # Activities
6694171 10.1021/jm00368a023 HT-29 2
110930 10.1021/jm00191a005 Thymidylate synthase 2
19419201 10.1021/jm800455g Influenza A virus 2
2704031 10.1021/jm00124a019 L1210 2
6694171 10.1021/jm00368a023 WiDr 2
6694171 10.1021/jm00368a023 SW480 2
6694171 10.1021/jm00368a023 Unchecked 2
3339615 10.1021/jm00397a031 Thymidylate synthase 1
3339615 10.1021/jm00397a031 Dihydrofolate reductase 1
2704031 10.1021/jm00124a019 Dihydrofolate reductase 1
2704031 10.1021/jm00124a019 Thymidylate synthase 1
3612694 10.1021/jm00391a042 HuTu80 1
3612694 10.1021/jm00391a042 HT-29 1
3612694 10.1021/jm00391a042 SW480 1
3612694 10.1021/jm00391a042 WiDr 1
19419201 10.1021/jm800455g ADMET 1
19419201 10.1021/jm800455g MDCK 1
110930 10.1021/jm00191a005 Dihydrofolate reductase 1

Data from ChEMBL 36 via Core Engine