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Compound Detail

CHEMBL1939876

BI 4394
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CCOC(=O)c1cc2cc(-c3cc(C(=O)NCc4ccc(C(=O)O)cc4)nn3C)ccc2[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1939876
Name BI 4394
Phase Preclinical
Structure Type MOL
InChI Key MMJPVSDTLGFIQW-UHFFFAOYSA-N
11
Targets
29
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

446.5
MW (Da)
3.37
ALogP
6
HBA
3
HBD
126.3
PSA (Ų)
0.37
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C24H22N4O5
MW 446.46
Aromatic Rings 4
Heavy Atoms 33
NP-Likeness -1.30

Activity Summary

IC50 27 meas. best 9.1
Ki 2 meas. best 5.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Collagenase 3
CHEMBL3638350
 IC50 9.1 9.1 0.8 1
Collagenase 3
CHEMBL280
 IC50 9.0 8.16 1.0 11
MAP kinase-activated protein kinase 2
CHEMBL2208
 IC50 5.96 5.96 1100.0 1
Aurora kinase A
CHEMBL4722
 IC50 5.89 5.89 1300.0 1
cAMP-dependent protein kinase catalytic subunit alpha
CHEMBL4101
 IC50 5.8 5.8 1600.0 1
5'-AMP-activated protein kinase catalytic subunit alpha-1
CHEMBL4045
 IC50 5.72 5.72 1900.0 1
Matrix metalloproteinase-14
CHEMBL3869
 IC50 5.08 5.08 8300.0 3
Matrix metalloproteinase-9
CHEMBL321
 IC50 5.05 5.05 8900.0 3
D(1B) dopamine receptor
CHEMBL1850
 Ki 5.0 5.0 10000.0 2
Stromelysin-2
CHEMBL4270
 IC50 4.8 4.8 16000.0 3
72 kDa type IV collagenase
CHEMBL333
 IC50 4.75 4.75 18000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1109.0 nM.hr/ml Rattus norvegicus
AUC 4328.0 nM.hr/ml Rattus norvegicus
CL 34.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 1657.0 nM Rattus norvegicus
F 39.0 % Rattus norvegicus
T1/2 0.47 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Collagenase 3 IC50 = 0.8 nM 9.1 Biological Assay: The EnzoLyte 520 Generic MMP Assay Kit (AnaSpec Inc.) can dete... -
Collagenase 3 IC50 = 1.0 nM 9.0 Inhibition of human MMP13 expressed in Escherichia coli after 30 mins by fluorim... 22017539
Collagenase 3 IC50 = 1.0 nM 9.0 Biochemical assay (FRET) with MMP13 -
Collagenase 3 IC50 = 1.0 nM 9.0 Affinity Biochemical interaction (FRET assay) EUB0000730a MMP13 -
Collagenase 3 IC50 = 4.0 nM 8.4 Inhibition of MMP13 after 30 mins by fluorimetry in the presence of 1.25% human ... 22017539
Collagenase 3 IC50 = 4.0 nM 8.4 Selectivity interaction (MMPs panel (FRET assay, + 1.25 % HSA)) EUB0000730a MMP1... -
Collagenase 3 IC50 = 11.0 nM 7.96 Inhibition of AMPA-activated MMP13-mediated degradation of FITC-labeled type2 co... 22017539
Collagenase 3 IC50 = 11.0 nM 7.96 MMP13 collagen degradation assay -
Collagenase 3 IC50 = 31.0 nM 7.51 Inhibition of human MMP13-mediated degradation of bovine nasal cartilage after 2... 22017539
Collagenase 3 IC50 = 31.0 nM 7.51 Bovine nasal cartilage (BNC) degradation assay -
Collagenase 3 IC50 = 31.0 nM 7.51 Bovine nasal cartilage (BNC) degradation assay -
Collagenase 3 IC50 = 31.0 nM 7.51 Affinity Phenotypic Cellular interaction (ELISA (bovine nasal cartilage (BNC) de... -
MAP kinase-activated protein kinase 2 IC50 = 1100.0 nM 5.96 Selectivity interaction (Enzyme panel (Invitrogen)) EUB0000730a MAPKAPK2 -
Aurora kinase A IC50 = 1300.0 nM 5.89 Selectivity interaction (Enzyme panel (Invitrogen)) EUB0000730a STK6 -
cAMP-dependent protein kinase catalytic subunit alpha IC50 = 1600.0 nM 5.8 Selectivity interaction (Enzyme panel (Invitrogen)) EUB0000730a PRKACA -
5'-AMP-activated protein kinase catalytic subunit alpha-1 IC50 = 1900.0 nM 5.72 Selectivity interaction (Enzyme panel (Invitrogen)) EUB0000730a PRKAA1 -
Matrix metalloproteinase-14 IC50 = 8300.0 nM 5.08 Inhibition of human recombinant MMP14 after 60 mins by fluorimetry 22017539
Matrix metalloproteinase-14 IC50 = 8300.0 nM 5.08 Biochemical assay (FRET) with MMP14 -
Matrix metalloproteinase-14 IC50 = 8300.0 nM 5.08 Selectivity interaction (MMPs panel (FRET assay)) EUB0000730a MMP14 -
Matrix metalloproteinase-9 IC50 = 8900.0 nM 5.05 Inhibition of human recombinant MMP9 after 30 mins by fluorimetry 22017539

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4507281 Tyrosine-protein kinase ABL1 16
- 10.6019/CHEMBL4507281 Epidermal growth factor receptor 13
- 10.6019/CHEMBL4507281 Receptor-type tyrosine-protein kinase FLT3 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL4689842 Fibroblast 10
- 10.6019/CHEMBL4507281 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 10
- 10.6019/CHEMBL4507281 Mast/stem cell growth factor receptor Kit 10
- 10.6019/CHEMBL4689842 U2OS 9
22017539 10.1021/jm201129m Unchecked 8
- 10.6019/CHEMBL5303304 Fibroblast 8
- 10.6019/CHEMBL4689842 HEK-293T 8
22017539 10.1021/jm201129m Rattus norvegicus 7
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.6019/CHEMBL5303304 U2OS 5
- 10.6019/CHEMBL5303304 HEK-293T 5
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
- 10.6019/CHEMBL4507281 Proto-oncogene tyrosine-protein kinase receptor Ret 5
- 10.6019/CHEMBL4507281 Collagenase 3 4
22017539 10.1021/jm201129m Collagenase 3 4

Data from ChEMBL 36 via Core Engine