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Compound Detail

CHEMBL4165749

BI 2545
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O=C(NC[C@@H]1[C@H]2CN(C(=O)OCc3cc(C(F)(F)F)cc(C(F)(F)F)c3)C[C@@H]12)c1ccc2[nH]nnc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4165749
Name BI 2545
Phase Preclinical
Structure Type MOL
InChI Key ZDOBSAPHUUUOHX-OSYLJGHBSA-N
7
Targets
19
Activities
2
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

527.4
MW (Da)
4.24
ALogP
5
HBA
2
HBD
100.2
PSA (Ų)
0.48
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C23H19F6N5O3
MW 527.43
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -1.14

Activity Summary

IC50 11 meas. best 8.66
Ki 8 meas. best 5.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Autotaxin
CHEMBL3691
 IC50 8.66 8.1 2.2 6
Autotaxin
CHEMBL3826870
 IC50 8.47 7.745 3.4 4
Rattus norvegicus
CHEMBL376
 IC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 Ki 5.62 5.605 2398.8 2
4-aminobutyrate aminotransferase, mitochondrial
CHEMBL2044
 Ki 5.59 5.59 2560.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 5.45 5.45 3548.1 3
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.06 5.06 8676.7 2

Pharmacokinetic Data

Parameter Value Units Species
CL 10.0 % Rattus norvegicus
F 30.0 % Rattus norvegicus
T1/2 1.8 hr Rattus norvegicus
T1/2 3.4 hr Rattus norvegicus
Tmax 1.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Autotaxin IC50 = 2.2 nM 8.66 Biochemical assay: measurement of LPA (human) -
Autotaxin IC50 = 2.2 nM 8.66 Affinity Biochemical interaction: (Biochemical assay (LPA measurement)) EUB00003... -
Autotaxin IC50 = 2.2 nM 8.66 Inhibition of human ATX 29259743
Autotaxin IC50 = 3.4 nM 8.47 Inhibition of recombinant rat ATX using LPC 18:1 as substrate after 2 hrs by rap... 29259743
Autotaxin IC50 = 3.4 nM 8.47 Biochemical assay: measurement of LPA (rat) -
Autotaxin IC50 = 29.0 nM 7.54 Inhibition of ATX in human whole blood 29259743
Autotaxin IC50 = 29.0 nM 7.54 Whole blood assay: measurement of LPA (human) -
Autotaxin IC50 = 29.0 nM 7.54 Affinity On-target Cellular interaction: (Inhibition of Autotaxin, whole blood a... -
Autotaxin IC50 = 96.0 nM 7.02 Whole blood assay: measurement of LPA (rat) -
Autotaxin IC50 = 96.0 nM 7.02 Inhibition of ATX in rat whole blood using LPA 17:0 as substrate after 1 hr by L... 29259743
Rattus norvegicus IC50 = 100.0 nM 7.0 In vivo inhibition of ATX in Han Wistar rat assessed as decrease in plasma LPA s... 29259743
Unchecked Ki = 2398.83 nM 5.62 GPCRScan assay: inhibition of GABA/PBR -
Unchecked Ki = 2555.91 nM 5.59 GPCRScan assay: inhibition of GABA/PBR -
4-aminobutyrate aminotransferase, mitochondrial Ki = 2560.0 nM 5.59 Selectivity interaction (GPCR panel (PDSP screen)) EUB0000318b ABAT -
Sigma non-opioid intracellular receptor 1 Ki = 3551.58 nM 5.45 GPCRScan assay: inhibition of Sigma 1 -
Sigma non-opioid intracellular receptor 1 Ki = 3548.13 nM 5.45 GPCRScan assay: inhibition of Sigma 1 -
Sigma non-opioid intracellular receptor 1 Ki = 3550.0 nM 5.45 Selectivity interaction (GPCR panel (PDSP screen)) EUB0000318b SIGMAR1 -
5-hydroxytryptamine receptor 2A Ki = 8676.68 nM 5.06 GPCRScan assay: inhibition of 5-HT2A -
5-hydroxytryptamine receptor 2A Ki = 8709.64 nM 5.06 GPCRScan assay: inhibition of 5-HT2A -

Literature References

PubMed DOI Target Context # Activities
29259743 10.1021/acsmedchemlett.7b00312 Rattus norvegicus 15
- 10.6019/CHEMBL4507275 Tyrosine-protein kinase ABL1 15
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL4507275 Epidermal growth factor receptor 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL4507275 Receptor-type tyrosine-protein kinase FLT3 11
- 10.6019/CHEMBL4507275 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 10
- 10.6019/CHEMBL4507275 Unchecked 10
- 10.6019/CHEMBL4507275 Mast/stem cell growth factor receptor Kit 9
- 10.6019/CHEMBL5303304 HEK-293T 8
- 10.6019/CHEMBL5058564 Fibroblast 8
- 10.6019/CHEMBL5058564 HEK-293T 7
- 10.6019/CHEMBL5303304 Fibroblast 6
- 10.6019/CHEMBL5303304 U2OS 6
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
29259743 10.1021/acsmedchemlett.7b00312 ADMET 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
- 10.6019/CHEMBL4507275 5-hydroxytryptamine receptor 2A 4
- 10.6019/CHEMBL4507275 Autotaxin 4
29259743 10.1021/acsmedchemlett.7b00312 Autotaxin 4

Data from ChEMBL 36 via Core Engine