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Compound Detail

CHEMBL170758

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CCC(CC)n1c(C)cc2c3c(N)nc(N)nc3ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL170758
Phase Preclinical
Structure Type MOL
InChI Key YBHNZQJIFKDDHM-UHFFFAOYSA-N
15
Targets
18
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

283.4
MW (Da)
3.42
ALogP
5
HBA
2
HBD
82.8
PSA (Ų)
0.77
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H21N5
MW 283.38
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -0.98

Activity Summary

IC50 14 meas. best 9.92
Ki 4 meas. best 10.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL2329
 Ki 10.52 10.52 0.0 2
P388
CHEMBL389
 IC50 9.92 9.92 0.1 1
Dihydrofolate reductase
CHEMBL202
 Ki 9.52 9.52 0.3 1
A549
CHEMBL392
 IC50 9.4 9.4 0.4 1
NCI-H460
CHEMBL396
 IC50 9.3 9.3 0.5 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.22 8.93 0.6 2
HCT-8
CHEMBL613510
 IC50 9.13 9.13 0.7 1
143B
CHEMBL614508
 IC50 9.1 9.1 0.8 1
Vero
CHEMBL391
 IC50 9.0 9.0 1.0 1
U-87 MG
CHEMBL614247
 IC50 8.68 8.68 2.1 1
U373 MG
CHEMBL615024
 IC50 8.64 8.64 2.3 1
D54 cell line
CHEMBL612247
 IC50 8.34 8.34 4.6 1
Glucose transporter
CHEMBL3431938
 IC50 5.86 5.86 1390.0 1
Hexose transporter 1
CHEMBL4697
 IC50 5.83 5.83 1482.0 1
Solute carrier family 2, facilitated glucose transporter member 1
CHEMBL2535
 IC50 5.69 5.69 2022.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 599.9 nM Canis lupus familiaris
F 49.0 % Canis lupus familiaris
T1/2 4.0 hr Canis lupus familiaris
T1/2 2.8 hr Canis lupus familiaris
Tmax 1.8 hr Canis lupus familiaris
Vd 9.3 L.kg-1 Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 0.03 nM 10.52 Competitive inhibition of Candida albicans DHFR preincubated for 2 mins followed... 25937878
Dihydrofolate reductase Ki = 0.03 nM 10.52 Inhibition of Dihydrofolate reductase enzyme from Candida albicans 8632413
P388 IC50 = 0.12 nM 9.92 Cytotoxic activity was evaluated against P388D1 tumor cells 8632413
Dihydrofolate reductase Ki = 0.3 nM 9.52 Inhibition of human recombinant Dihydrofolate reductase enzyme 8632413
A549 IC50 = 0.4 nM 9.4 Cytotoxic activity evaluated against A549 tumor cells 8632413
NCI-H460 IC50 = 0.5 nM 9.3 Cytotoxic Activity was evaluated against H460 tumor cells 8632413
NON-PROTEIN TARGET IC50 = 0.6 nM 9.22 Cytotoxic activity was evaluated against L tumor cells 8632413
HCT-8 IC50 = 0.74 nM 9.13 Activity was evaluated against HCT-8 tumor cells 8632413
143B IC50 = 0.8 nM 9.1 Cytotoxic Activity was evaluated against 143B (TK-) tumor cells 8632413
Vero IC50 = 1.0 nM 9.0 Cytotoxic Activity was evaluated against Vero tumor cells 8632413
U-87 MG IC50 = 2.1 nM 8.68 Cytotoxic activity was evaluated against U87MG tumor cells 8632413
NON-PROTEIN TARGET IC50 = 2.3 nM 8.64 Cytotoxic activity was evaluated against Daoy tumor cells 8632413
U373 MG IC50 = 2.3 nM 8.64 Cytotoxic activity was evaluated against U373MG tumor cells 8632413
D54 cell line IC50 = 4.6 nM 8.34 Cytotoxic Activity was evaluated against D54 tumor cells 8632413
Glucose transporter IC50 = 1390.0 nM 5.86 ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes... -
Hexose transporter 1 IC50 = 1482.0 nM 5.83 ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes... -
Solute carrier family 2, facilitated glucose transporter member 1 IC50 = 2022.0 nM 5.69 ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes... -

Literature References

PubMed DOI Target Context # Activities
8632413 10.1021/jm9505122 Mus musculus 10
25937878 10.1039/c4md00485j Canis familiaris 6
8632413 10.1021/jm9505122 P388 4
20485427 10.1038/nature09107 Plasmodium falciparum 4
8632413 10.1021/jm9505122 MCF7 3
- 10.6019/CHEMBL3433997 Hexose transporter 1 2
- 10.6019/CHEMBL3433997 Glucose transporter 2
8632413 10.1021/jm9505122 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL3433997 Solute carrier family 2, facilitated glucose transporter member 1 2
25937878 10.1039/c4md00485j Dihydrofolate reductase 2
8632413 10.1021/jm9505122 Dihydrofolate reductase 2
8632413 10.1021/jm9505122 KB 2
8632413 10.1021/jm9505122 U373 MG 1
8632413 10.1021/jm9505122 Rattus norvegicus 1
8632413 10.1021/jm9505122 Vero 1
25937878 10.1039/c4md00485j Candida albicans 1
8632413 10.1021/jm9505122 A549 1
8632413 10.1021/jm9505122 U-87 MG 1
8632413 10.1021/jm9505122 D54 cell line 1
8632413 10.1021/jm9505122 HCT-8 1

Data from ChEMBL 36 via Core Engine