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Compound Detail

CHEMBL4457578

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Cc1c(-c2cccc(S(=O)(=O)N(C)C)c2)c2cc(C(=O)O)ccc2n1C/C(F)=C/CN.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4457578
Phase Preclinical
Structure Type MOL
InChI Key PWSRWJMEGVKWES-WPTDRQDKSA-N
Parent Compound CHEMBL4534495
Active Moiety CHEMBL4534495
9
Targets
15
Activities
2
Assay Types
11
PK Parameters
11
Publications
0
Known Names

Molecular Properties

445.5
MW (Da)
3.38
ALogP
5
HBA
2
HBD
105.6
PSA (Ų)
0.58
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H25ClFN3O4S
MW 481.98
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.08

Activity Summary

IC50 14 meas. best 8.4
Ki 1 meas. best 7.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysyl oxidase homolog 2
CHEMBL3714029
 IC50 8.4 8.106 4.0 5
Lysyl oxidase homolog 2
CHEMBL4105831
 IC50 8.22 8.22 6.0 1
Lysyl oxidase homolog 2
CHEMBL4105908
 IC50 8.22 8.22 6.0 1
Lysyl oxidase homolog 3
CHEMBL4105989
 IC50 7.8 7.8 16.0 1
Lysyl oxidase homolog 2
CHEMBL3714029
 Ki 7.08 7.08 83.0 1
Lysyl oxidase homolog 4
CHEMBL4295926
 IC50 6.55 6.55 280.0 1
Protein-lysine 6-oxidase
CHEMBL2249
 IC50 5.9 5.9 1260.0 1
Protein-lysine 6-oxidase
CHEMBL4523217
 IC50 5.8 5.775 1584.9 2
Protein-lysine 6-oxidase
CHEMBL4523209
 IC50 5.76 5.76 1754.0 1
Lysyl oxidase homolog 1
CHEMBL4523279
 IC50 5.65 5.65 2260.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 1.0 % Rattus norvegicus
F 1.0 % Mus musculus
T1/2 2.0 hr Rattus norvegicus
T1/2 2.0 hr Canis lupus familiaris
T1/2 2.0 hr Homo sapiens
T1/2 1.5 hr Rattus norvegicus
T1/2 1.5 hr Canis lupus familiaris
T1/2 1.5 hr Homo sapiens
T1/2 2.0 hr Rattus norvegicus
T1/2 2.0 hr Canis lupus familiaris
T1/2 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysyl oxidase homolog 2 IC50 = 3.981 nM 8.4 Inhibition of recombinant human C-terminal His-tagged LOLX2 (1-774 residues) exp... 31580073
Lysyl oxidase homolog 2 IC50 = 5.0 nM 8.3 Inhibition of recombinant human C-terminal His-tagged LOLX2 (1-774 residues) exp... 31580073
Lysyl oxidase homolog 2 IC50 = 6.0 nM 8.22 Inhibition of recombinant mouse C-terminal His-tagged LOLX2 (26-776 residues) ex... 31580073
Lysyl oxidase homolog 2 IC50 = 6.0 nM 8.22 Inhibition of recombinant rat LOLX2 using putrescine as substrate preincubated w... 31580073
Lysyl oxidase homolog 2 IC50 = 9.0 nM 8.05 Inhibition of LOXL2 in human IMR90 cells using putrescine as substrate preincuba... 31580073
Lysyl oxidase homolog 2 IC50 = 13.0 nM 7.89 Inhibition of recombinant human LOXL2 assessed as inhibition of collagen cross l... 31580073
Lysyl oxidase homolog 2 IC50 = 13.0 nM 7.89 Inhibition of recombinant human C-terminal His-tagged LOLX2 (1-774 residues) exp... 31580073
Lysyl oxidase homolog 3 IC50 = 16.0 nM 7.8 Inhibition of recombinant C-terminal His-tagged human LOXL3 (1 to 753 residues) ... 31580073
Lysyl oxidase homolog 2 Ki = 83.0 nM 7.08 Time-dependent inhibition of recombinant human C-terminal His-tagged LOLX2 (1-77... 31580073
Lysyl oxidase homolog 4 IC50 = 280.0 nM 6.55 Inhibition of recombinant human LOXL4 using putrescine as substrate preincubated... 31580073
Protein-lysine 6-oxidase IC50 = 1260.0 nM 5.9 Inhibition of LOX in human IMR90 cells using putrescine as substrate preincubate... 31580073
Protein-lysine 6-oxidase IC50 = 1584.89 nM 5.8 Inhibition of LOX in bovine aorta using putrescine as substrate preincubated wit... 31580073
Protein-lysine 6-oxidase IC50 = 1754.0 nM 5.76 Inhibition of LOX in mouse lung fibroblast cells using putrescine as substrate p... 31580073
Protein-lysine 6-oxidase IC50 = 1780.0 nM 5.75 Inhibition of LOX in bovine aorta using putrescine as substrate preincubated wit... 31580073
Lysyl oxidase homolog 1 IC50 = 2260.0 nM 5.65 Inhibition of recombinant human LOXL1 using putrescine as substrate preincubated... 31580073

Literature References

PubMed DOI Target Context # Activities
31580073 10.1021/acs.jmedchem.9b01283 Lysyl oxidase homolog 2 14
31580073 10.1021/acs.jmedchem.9b01283 ADMET 14
31580073 10.1021/acs.jmedchem.9b01283 Protein-lysine 6-oxidase 4
31580073 10.1021/acs.jmedchem.9b01283 Unchecked 3
31580073 10.1021/acs.jmedchem.9b01283 Amine oxidase [copper-containing] 3 2
31580073 10.1021/acs.jmedchem.9b01283 Amine oxidase [flavin-containing] A 1
31580073 10.1021/acs.jmedchem.9b01283 Amine oxidase [flavin-containing] B 1
31580073 10.1021/acs.jmedchem.9b01283 D-amino-acid oxidase 1
31580073 10.1021/acs.jmedchem.9b01283 Lysyl oxidase homolog 1 1
31580073 10.1021/acs.jmedchem.9b01283 Lysyl oxidase homolog 3 1
31580073 10.1021/acs.jmedchem.9b01283 Lysyl oxidase homolog 4 1

Data from ChEMBL 36 via Core Engine