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Compound Detail

CHEMBL2180727

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Cc1ccccc1C(C(=O)NC1CCCCC1)N(C(=O)Cn1ccnc1C)c1cccc(F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2180727
Phase Preclinical
Structure Type MOL
InChI Key FNYGWXSATBUBER-UHFFFAOYSA-N
2
Targets
21
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

462.6
MW (Da)
4.86
ALogP
4
HBA
1
HBD
67.2
PSA (Ų)
0.55
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H31FN4O2
MW 462.57
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.92

Activity Summary

IC50 16 meas. best 7.7
Kd 4 meas. best 5.07
EC50 1 meas. best 7.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Isocitrate dehydrogenase [NADP] cytoplasmic
CHEMBL2007625
 IC50 7.7 6.9167 20.0 15
Isocitrate dehydrogenase [NADP] cytoplasmic
CHEMBL2007625
 EC50 7.22 7.22 60.0 1
Isocitrate dehydrogenase [NADP] cytoplasmic
CHEMBL2007625
 Kd 5.07 4.7067 8600.0 3
U-87 MG
CHEMBL614247
 IC50 4.7 4.7 20100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 20800.0 ng.hr.mL-1 Mus musculus
Fu 0.043 - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 20.0 nM 7.7 Inhibition of recombinant human N-terminal GST-fused IDH1 R132H mutant expressed... 30600148
Isocitrate dehydrogenase [NADP] cytoplasmic EC50 = 60.0 nM 7.22 Inhibition of IDH1-R132H mutant (unknown origin) expressed in human HA1EM cells ... 27774134
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 61.0 nM 7.21 Inhibition of recombinant IDH1 R132H mutant (unknown origin) expressed in Escher... 36952395
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 70.0 nM 7.16 Inhibition of IDH1 R132H mutant expressed in human U87 cells assessed as inhibit... 24900389
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 70.0 nM 7.16 Inhibition of IDH1 R132H mutant using alpha-ketoglutarate as substrate after 60 ... 24900389
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 70.0 nM 7.16 Inhibition of IDH1 R132H mutant (unknown origin) 29089260
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 80.0 nM 7.1 Inhibition of His-tagged recombinant human IDH1 R132H mutant expressed in Escher... 30108937
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 82.0 nM 7.09 Inhibition of N-terminal 6-His-tagged IDH1 R132H mutant (unknown origin) express... 31208797
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 160.0 nM 6.8 Inhibition of IDH1 R132C mutant using alpha-ketoglutarate as substrate after 60 ... 24900389
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 160.0 nM 6.8 Inhibition of IDH1 R132C mutant (unknown origin) 29089260
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 170.0 nM 6.77 Inhibition of IDH1 R132H mutant (unknown origin) 32143887
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 186.1 nM 6.73 Inhibition of recombinant human N-terminal GST-fused IDH1 R132L mutant expressed... 30600148
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 200.0 nM 6.7 Inhibition of IDH1 R132H mutant (unknown origin) assessed as reduction in NADPH ... 31674782
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 226.8 nM 6.64 Inhibition of recombinant human N-terminal GST-fused IDH1 R132C mutant expressed... 30600148
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 390.0 nM 6.41 Inhibition of IDH1 R132C mutant (unknown origin) 32143887
Isocitrate dehydrogenase [NADP] cytoplasmic IC50 = 480.0 nM 6.32 Inhibition of IDH1 R132C mutant overexpressed in human HT1080 cells assessed as ... 24900389
Isocitrate dehydrogenase [NADP] cytoplasmic Kd = 8600.0 nM 5.07 Binding affinity to recombinant IDH1 R132H mutant (unknown origin) expressed in ... 36952395
Isocitrate dehydrogenase [NADP] cytoplasmic Kd = 9100.0 nM 5.04 Binding affinity to recombinant wildtype IDH1 (unknown origin) expressed in Esch... 36952395
U-87 MG IC50 = 20100.0 nM 4.7 Antiproliferative activity against human U87 cells by MTT assay 30108937
Isocitrate dehydrogenase [NADP] cytoplasmic Kd = 98000.0 nM 4.01 Binding affinity to human recombinant IDH1 R132H mutant expressed in Escherichia... 36952395

Literature References

PubMed DOI Target Context # Activities
36952395 10.1021/acs.jmedchem.3c00203 Isocitrate dehydrogenase [NADP] cytoplasmic 22
25271760 10.1021/jm500660f Unchecked 7
24900389 10.1021/ml300225h Isocitrate dehydrogenase [NADP] cytoplasmic 5
24900389 10.1021/ml300225h Mus musculus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
29290542 10.1016/j.bmcl.2017.12.030 Isocitrate dehydrogenase [NADP] cytoplasmic 4
30600148 10.1016/j.bmc.2018.12.029 Isocitrate dehydrogenase [NADP] cytoplasmic 4
30108937 10.1039/C7MD00551B HT-1080 3
30108937 10.1039/C7MD00551B U-87 MG 3
32143887 10.1016/j.bmcl.2020.127070 Isocitrate dehydrogenase [NADP] cytoplasmic 3
25271760 10.1021/jm500660f MDCK 3
32143887 10.1016/j.bmcl.2020.127070 Isocitrate dehydrogenase [NADP], mitochondrial 3
27774134 10.1021/acsmedchemlett.6b00264 Isocitrate dehydrogenase [NADP] cytoplasmic 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
30108937 10.1039/C7MD00551B Isocitrate dehydrogenase [NADP] cytoplasmic 2
29089260 10.1016/j.bmc.2017.10.009 Isocitrate dehydrogenase [NADP] cytoplasmic 2
26280302 10.1021/acs.jmedchem.5b00684 ADMET 2
30600148 10.1016/j.bmc.2018.12.029 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
24900389 10.1021/ml300225h Liver microsomes 2

Data from ChEMBL 36 via Core Engine