Compound Detail

CHEMBL187092

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C[C@@]1(O)CCCN(S(=O)(=O)c2ccc(OCc3ccc(F)cc3Cl)cc2)[C@H]1C(=O)NO

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL187092
Phase	Preclinical
Structure Type	MOL
InChI Key	LTVIJEFEZVFIST-AZUAARDMSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

472.9

MW (Da)

2.47

ALogP

HBA

HBD

116.2

PSA (Å²)

0.44

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C20H22ClFN2O6S
MW	472.92
Aromatic Rings	2
Heavy Atoms	31
NP-Likeness	-1.14

Activity Summary

IC50 36 meas. best 9.05

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Collagenase 3 CHEMBL280	IC50	9.05	9.0167	0.9	3
Unchecked CHEMBL612545	IC50	9.05	8.8967	0.9	3
A disintegrin and metalloproteinase with thrombospondin motifs 5 CHEMBL2285	IC50	9.0	8.34	1.0	5
A disintegrin and metalloproteinase with thrombospondin motifs 4 CHEMBL2318	IC50	9.0	8.84	1.0	3
Neutrophil collagenase CHEMBL4588	IC50	9.0	9.0	1.0	1
Disintegrin and metalloproteinase domain-containing protein 17 CHEMBL3706	IC50	8.8	7.3167	1.6	3
Stromelysin-1 CHEMBL283	IC50	8.52	8.4467	3.0	3
72 kDa type IV collagenase CHEMBL333	IC50	8.4	8.3333	4.0	3
Cell line CHEMBL614840	IC50	8.22	8.22	6.0	1
Bos taurus CHEMBL613489	IC50	7.99	7.495	10.3	2
Tumor necrosis factor CHEMBL1825	IC50	7.98	7.98	10.4	1
Matrix metalloproteinase-9 CHEMBL321	IC50	7.96	7.96	11.0	1
A disintegrin and metalloproteinase with thrombospondin motifs 1 CHEMBL5133	IC50	7.1	7.1	79.0	1
Matrix metalloproteinase-14 CHEMBL3869	IC50	7.08	6.9067	83.0	3
Interstitial collagenase CHEMBL332	IC50	6.7	6.5733	200.0	3

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	13.0	mL.min-1.kg-1	Rattus norvegicus
CL	11.0	mL.min-1.kg-1	Canis lupus familiaris
T1/2	2.0	hr	Rattus norvegicus
T1/2	4.6	hr	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Collagenase 3	IC50	=	0.9	nM	9.05	Inhibition of MMP-13 using 5-FAM-TPGPLGL[Dap- (DNP)]ARRK(5-TAMRA)-amide as subst...	22891645
Unchecked	IC50	=	0.9	nM	9.05	Inhibitory concentration against MMP-13	15953722
Neutrophil collagenase	IC50	=	1.0	nM	9.0	Inhibitory concentration against MMP-8	15953722
A disintegrin and metalloproteinase with thrombospondin motifs 4	IC50	=	1.0	nM	9.0	Inhibition of human ADAMTS-4 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p...	25415648
A disintegrin and metalloproteinase with thrombospondin motifs 5	IC50	=	1.0	nM	9.0	Inhibition of human ADAMTS-5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p...	25415648
Collagenase 3	IC50	=	1.0	nM	9.0	Inhibition of human MMP13 using Mca-PQG1 peptide substrate assessed as substrate...	25415648
A disintegrin and metalloproteinase with thrombospondin motifs 4	IC50	=	1.0	nM	9.0	Inhibition of human ADAMTS4 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG pe...	28613895
A disintegrin and metalloproteinase with thrombospondin motifs 5	IC50	=	1.0	nM	9.0	Inhibition of human ADAMTS5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG pe...	28613895
Collagenase 3	IC50	=	1.0	nM	9.0	Inhibition of human MMP13 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminop...	28613895
Unchecked	IC50	=	1.5	nM	8.82	Inhibitory concentration against aggrecanase from porcine chondrocytes using [35...	15953722
Unchecked	IC50	=	1.5	nM	8.82	Inhibition of aggrecanase	22891645
Disintegrin and metalloproteinase domain-containing protein 17	IC50	=	1.6	nM	8.8	Inhibition of TACE using Mca-PLAQAV-Dpa-RSSSR-NH2 as substrate preincubated 15 m...	22891645
A disintegrin and metalloproteinase with thrombospondin motifs 4	IC50	=	3.0	nM	8.52	Inhibition of ADAMTS-4 using WAAG-3R as substrate preincubated for 15 mins measu...	22891645
Stromelysin-1	IC50	=	3.0	nM	8.52	Inhibition of human MMP3 using Mca-PQG1 peptide substrate assessed as substrate ...	25415648
Stromelysin-1	IC50	=	3.0	nM	8.52	Inhibition of human MMP3 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminopr...	28613895
72 kDa type IV collagenase	IC50	=	4.0	nM	8.4	Inhibitory concentration against MMP-2	15953722
72 kDa type IV collagenase	IC50	=	5.0	nM	8.3	Inhibition of human MMP2 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminopr...	28613895
Stromelysin-1	IC50	=	5.0	nM	8.3	Inhibitory concentration against MMP-3	15953722
72 kDa type IV collagenase	IC50	=	5.0	nM	8.3	Inhibition of human MMP2 using Mca-PQG1 peptide substrate assessed as substrate ...	25415648
Cell line	IC50	=	6.0	nM	8.22	Inhibition of IL-1 induced aggrecan degradation in human osteoarthritic cartilag...	15953722

Literature References

PubMed	DOI	Target Context	# Activities
15953722	10.1016/j.bmcl.2005.05.037	ADMET	4
25415648	10.1021/jm501522n	A disintegrin and metalloproteinase with thrombospondin motifs 5	2
25415648	10.1021/jm501522n	Plasma	2
28613895	10.1021/acs.jmedchem.7b00650	A disintegrin and metalloproteinase with thrombospondin motifs 5	2
15953722	10.1016/j.bmcl.2005.05.037	Cricetinae gen. sp.	2
28613895	10.1021/acs.jmedchem.7b00650	Rattus norvegicus	2
15953722	10.1016/j.bmcl.2005.05.037	Bos taurus	2
27194201	10.1021/acs.jmedchem.6b00398	Rattus norvegicus	2
15953722	10.1016/j.bmcl.2005.05.037	Unchecked	2
15953722	10.1016/j.bmcl.2005.05.037	72 kDa type IV collagenase	1
22891645	10.1021/jm300449x	A disintegrin and metalloproteinase with thrombospondin motifs 4	1
22891645	10.1021/jm300449x	Unchecked	1
22891645	10.1021/jm300449x	Collagenase 3	1
22891645	10.1021/jm300449x	Interstitial collagenase	1
22891645	10.1021/jm300449x	Disintegrin and metalloproteinase domain-containing protein 17	1
15953722	10.1016/j.bmcl.2005.05.037	Stromelysin-1	1
15953722	10.1016/j.bmcl.2005.05.037	Tumor necrosis factor	1
15953722	10.1016/j.bmcl.2005.05.037	Interstitial collagenase	1
15953722	10.1016/j.bmcl.2005.05.037	Matrix metalloproteinase-14	1
15953722	10.1016/j.bmcl.2005.05.037	Matrix metalloproteinase-9	1

Data from ChEMBL 36 via Core Engine