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Compound Detail

CHEMBL18155

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Nc1nc(N)c2nc(CNc3ccc(C(=O)NC(CCCNC(=O)c4ccccc4C(=O)O)C(=O)O)cc3)cnc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL18155
Phase Preclinical
Structure Type MOL
InChI Key NYQPLPNEESYGNO-UHFFFAOYSA-N
47
Targets
86
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

573.6
MW (Da)
1.29
ALogP
11
HBA
7
HBD
248.4
PSA (Ų)
0.12
QED
3
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H27N9O6
MW 573.57
Aromatic Rings 4
Heavy Atoms 42
NP-Likeness -0.62

Activity Summary

IC50 81 meas. best 9.74
Ki 5 meas. best 10.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydrofolate reductase
CHEMBL4564
 Ki 10.38 8.985 0.0 2
HCT-116
CHEMBL394
 IC50 9.74 9.63 0.2 2
LOX IMVI
CHEMBL614096
 IC50 9.64 9.52 0.2 2
SCC-25
CHEMBL614901
 IC50 9.52 9.26 0.3 2
K562
CHEMBL385
 IC50 9.52 9.52 0.3 1
HL-60
CHEMBL383
 IC50 9.39 9.39 0.4 1
SR
CHEMBL614300
 IC50 9.38 9.38 0.4 1
NCI-H460
CHEMBL396
 IC50 9.37 9.335 0.4 2
786-0
CHEMBL613102
 IC50 9.3 9.26 0.5 2
SF-295
CHEMBL614908
 IC50 9.29 9.29 0.5 1
OVCAR-8
CHEMBL612555
 IC50 9.28 8.95 0.5 2
UACC-62
CHEMBL614610
 IC50 9.25 8.995 0.6 2
A549
CHEMBL392
 IC50 9.24 9.065 0.6 2
HCT-15
CHEMBL612263
 IC50 9.22 9.07 0.6 2
MCF7
CHEMBL387
 IC50 9.15 8.6767 0.7 3
SF-268
CHEMBL613977
 IC50 9.14 8.87 0.7 2
L1210
CHEMBL386
 IC50 9.12 9.12 0.8 2
ACHN
CHEMBL614519
 IC50 9.09 8.855 0.8 2
SCC-7
CHEMBL614147
 IC50 9.05 9.05 0.9 1
Molecular identity unknown
CHEMBL612546
 IC50 9.02 8.8175 1.0 4
OVCAR-5
CHEMBL614214
 IC50 9.0 8.8 1.0 2
CCRF-CEM
CHEMBL382
 IC50 8.97 8.3925 1.1 4
Dihydrofolate reductase
CHEMBL202
 IC50 8.96 8.435 1.1 2
HT-29
CHEMBL384
 IC50 8.92 8.92 1.2 1
HCC 2998
CHEMBL613855
 IC50 8.89 8.89 1.3 1
Unchecked
CHEMBL612545
 IC50 8.74 8.03 1.8 2
SW-620
CHEMBL612262
 IC50 8.72 8.72 1.9 1
Malme-3M
CHEMBL614021
 IC50 8.7 8.7 2.0 2
KM12
CHEMBL614709
 IC50 8.66 8.575 2.2 2
SF-539
CHEMBL614860
 IC50 8.64 8.535 2.3 2
NCI-H23
CHEMBL614997
 IC50 8.59 8.475 2.6 2
NCI/ADR-RES
CHEMBL613829
 IC50 8.57 8.57 2.7 2
MDA-MB-435
CHEMBL614697
 IC50 8.51 8.51 3.1 1
SK-MEL-28
CHEMBL614919
 IC50 8.34 8.34 4.6 2
SK-MEL-5
CHEMBL614922
 IC50 8.33 8.275 4.7 2
U-251
CHEMBL615022
 IC50 8.28 8.28 5.2 1
MOLT-4
CHEMBL614177
 IC50 8.28 8.28 5.2 1
UO-31
CHEMBL614388
 IC50 8.26 8.26 5.5 1
NCI-H522
CHEMBL614387
 IC50 8.19 7.915 6.5 2
HOP-92
CHEMBL613889
 IC50 8.12 8.12 7.5 1
RXF 393
CHEMBL614886
 IC50 8.07 8.07 8.6 1
DU-145
CHEMBL613508
 IC50 8.02 8.02 9.5 2
TK-10
CHEMBL614056
 IC50 8.02 8.02 9.6 1
EKVX
CHEMBL614487
 IC50 7.64 7.64 23.0 2
UACC-257
CHEMBL612796
 IC50 7.6 7.6 25.0 1
OVCAR-3
CHEMBL614213
 IC50 7.34 7.34 46.0 1
Dihydrofolate reductase
CHEMBL4564
 IC50 7.28 7.28 52.0 2
CCRF-CEM
CHEMBL382
 Ki 6.36 6.275 440.0 2
L1210 ( R81)
CHEMBL614710
 IC50 4.28 4.28 52000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydrofolate reductase Ki = 0.042 nM 10.38 Inhibitory constant for murine Wild-type dihydrofolate reductase (DHFR) 12825924
HCT-116 IC50 = 0.18 nM 9.74 Compound was evaluated for in vitro activity against HCT116 Colon cell lines (Hu... 9857098
LOX IMVI IC50 = 0.23 nM 9.64 Compound was evaluated for in vitro activity against LOXIMV1 Melanoma cell lines... 9857098
HCT-116 IC50 = 0.3 nM 9.52 The IC50 value was measured on HCT116 cell line in colon tumor type. 9022795
K562 IC50 = 0.3 nM 9.52 Compound was evaluated for in vitro activity against K562 leukemia cell lines (H... 9857098
SCC-25 IC50 = 0.3 nM 9.52 In vitro antitumor activity against SCC25 human head and neck squamous carcinoma... 9022795
LOX IMVI IC50 = 0.4 nM 9.4 The IC50 value was measured on LOX IMVI cell line in melanoma tumor ty 9022795
HL-60 IC50 = 0.41 nM 9.39 Compound was evaluated for in vitro activity against HL-60(TB) leukemia cell lin... 9857098
SR IC50 = 0.42 nM 9.38 Compound was evaluated for in vitro activity against SR leukemia cell lines (Hum... 9857098
NCI-H460 IC50 = 0.43 nM 9.37 Compound was evaluated for in vitro activity against NCI-H460 lung cancer cell l... 9857098
NCI-H460 IC50 = 0.5 nM 9.3 The IC50 value was measured on NCl-H460 cell line in NSCL tumor type 9022795
786-0 IC50 = 0.5 nM 9.3 Compound was evaluated for in vitro activity against 786-0 kidney cell lines (Hu... 9857098
SF-295 IC50 = 0.51 nM 9.29 Compound was evaluated for in vitro activity against SF-295 CNS cell lines (Huma... 9857098
OVCAR-8 IC50 = 0.53 nM 9.28 Compound was evaluated for in vitro activity against OVCAR-8 Ovary cell lines (H... 9857098
UACC-62 IC50 = 0.56 nM 9.25 Compound was evaluated for in vitro activity against UACC-62 Melanoma cell lines... 9857098
A549 IC50 = 0.57 nM 9.24 Compound was evaluated for in vitro activity against A549/ATCC lung cancer cell ... 9857098
HCT-15 IC50 = 0.6 nM 9.22 Compound was evaluated for in vitro activity against HCT-15 Colon cell lines (Hu... 9857098
786-0 IC50 = 0.6 nM 9.22 The IC50 value was measured on 786-0 cell line in ovarian tumor 9022795
MCF7 IC50 = 0.7 nM 9.15 Tested for inhibitory concentration against MCF-7 human breast carcinoma cell li... 8035423
SF-268 IC50 = 0.73 nM 9.14 Compound was evaluated for in vitro activity against SF-268 CNS cell lines (Huma... 9857098

Literature References

PubMed DOI Target Context # Activities
1995880 10.1021/jm00106a016 L1210 53
12825924 10.1021/jm034057i Dihydrofolate reductase 5
9022795 10.1021/jm9606453 Mus musculus 4
8035423 10.1021/jm00040a008 CCRF-CEM 4
3385730 10.1021/jm00402a013 Molecular identity unknown 4
8035423 10.1021/jm00040a008 Dihydrofolate reductase 3
8035423 10.1021/jm00040a008 Unchecked 2
9857098 10.1021/jm980477+ HOP-92 1
9857098 10.1021/jm980477+ SK-MEL-2 1
9857098 10.1021/jm980477+ M14 1
9857098 10.1021/jm980477+ NCI-H522 1
9857098 10.1021/jm980477+ NCI-H460 1
9857098 10.1021/jm980477+ NCI-H23 1
9857098 10.1021/jm980477+ NCI-H226 1
9857098 10.1021/jm980477+ A549 1
9857098 10.1021/jm980477+ SR 1
9857098 10.1021/jm980477+ MOLT-4 1
9857098 10.1021/jm980477+ K562 1
9857098 10.1021/jm980477+ HL-60 1
9857098 10.1021/jm980477+ CCRF-CEM 1

Data from ChEMBL 36 via Core Engine