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Compound Detail

CHEMBL589973

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CCCCNC(=O)c1ccc(Oc2ccc(CC(=O)O)cc2OC)c(NS(=O)(=O)c2ccc(Cl)cc2Cl)c1

Basic Information

ChEMBL ID CHEMBL589973
Phase Preclinical
Structure Type MOL
InChI Key DKSKRBVXRDGYAS-UHFFFAOYSA-N
10
Targets
24
Activities
2
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

581.5
MW (Da)
5.75
ALogP
6
HBA
3
HBD
131.0
PSA (Ų)
0.23
QED
2
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H26Cl2N2O7S
MW 581.47
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness -1.32

Activity Summary

IC50 19 meas. best 8.52
Ki 5 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin D2 receptor 2
CHEMBL5071
Ki 9.0 9.0 1.0 1
Chemoattractant receptor-homologous molecule expressed on Th2 cells
CHEMBL1075058
IC50 8.52 8.52 3.0 1
Prostaglandin D2 receptor 2
CHEMBL5071
IC50 8.52 8.16 3.0 7
Prostaglandin D2 receptor
CHEMBL4427
IC50 7.92 7.3329 12.0 7
Unchecked
CHEMBL612545
Ki 6.88 6.88 131.0 1
Prostaglandin D2 receptor
CHEMBL4427
Ki 6.83 6.83 148.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
IC50 5.96 5.96 1100.0 1
Bile salt export pump
CHEMBL6020
IC50 4.94 4.94 11500.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.87 4.87 13500.0 1
Thromboxane A2 receptor
CHEMBL2069
IC50 4.52 4.52 30000.0 1
Prostaglandin E2 receptor EP4 subtype
CHEMBL1836
Ki 4.36 4.36 44000.0 1
Prostaglandin E2 receptor EP2 subtype
CHEMBL1881
Ki 4.36 4.36 44000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 32800.0 ng.hr.mL-1 Homo sapiens
CL 20.0 mL.min-1.kg-1 Rattus norvegicus
CL 12.83 mL.min-1.kg-1 Canis lupus familiaris
CL 4.5 mL.min-1.kg-1 Macaca fascicularis
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
F 28.0 % Rattus norvegicus
F 60.0 % Canis lupus familiaris
F 39.0 % Macaca fascicularis
MRT 0.9 hr Rattus norvegicus
MRT 1.4 hr Canis lupus familiaris
MRT 1.3 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin D2 receptor 2 Ki = 1.0 nM 9.0 Inhibition of PGD2-induced CRTH2 receptor internalization of CD16 negative granu... 19804971
Chemoattractant receptor-homologous molecule expressed on Th2 cells IC50 = 3.0 nM 8.52 Displacement of [3H]-PGD2 from guinea pig CRTH2 receptor expressed in HEK293 cel... 19804971
Prostaglandin D2 receptor 2 IC50 = 3.0 nM 8.52 Displacement of [3H]PGD2 from human CRTH2 receptor expressed in 293 cells by sci... 22119474
Prostaglandin D2 receptor 2 IC50 = 3.0 nM 8.52 Displacement of [3H]-PGD2 from human CRTH2 receptor expressed in human HEK293 ce... 24900313
Prostaglandin D2 receptor 2 IC50 = 3.0 nM 8.52 Displacement of [3H]-PGD2 from human CRTH2 expressed in HEK293 cells in buffer s... 24825301
Prostaglandin D2 receptor 2 IC50 = 3.0 nM 8.52 Displacement of [3H]-PGD2 from human CRTH2 expressed in HEK 293 cells in presenc... 19804971
Prostaglandin D2 receptor IC50 = 12.0 nM 7.92 Displacement of [3H]-PGD2 from human DP receptor expressed in HEK 293 cells in p... 19804971
Prostaglandin D2 receptor IC50 = 12.0 nM 7.92 Displacement of [3H]PGD2 from human DP receptor expressed in 293 cells by scinti... 22119474
Prostaglandin D2 receptor IC50 = 12.0 nM 7.92 Displacement of [3H]-PGD2 from human Prostanoid DP receptor expressed in human H... 24900313
Prostaglandin D2 receptor IC50 = 12.0 nM 7.92 Displacement of [3H]-PGD2 from human DP receptor expressed in HEK293 cells in bu... 24825301
Prostaglandin D2 receptor 2 IC50 = 21.0 nM 7.68 Displacement of [3H]PGD2 from human CRTh2 receptor expressed in 293 cells by sci... 22119474
Prostaglandin D2 receptor 2 IC50 = 21.0 nM 7.68 Displacement of [3H]PGD2 from human CRTH2 receptor expressed in HEK293 cells by ... 22264478
Prostaglandin D2 receptor 2 IC50 = 21.0 nM 7.68 Displacement of [3H]-PGD2 from human CRTH2 receptor expressed in human HEK293 ce... 24900313
Unchecked Ki = 131.0 nM 6.88 Inhibition of guinea pig DP receptor expressed in HEK 293 cells assessed as inhi... 19804971
Prostaglandin D2 receptor Ki = 148.0 nM 6.83 Antagonist activity at DP receptor in human platelets assessed as inhibition of ... 19804971
Prostaglandin D2 receptor IC50 = 280.0 nM 6.55 Displacement of [3H]PGD2 from human DP receptor expressed in 293 cells by scinti... 22119474
Prostaglandin D2 receptor IC50 = 280.0 nM 6.55 Displacement of [3H]-PGD2 from human Prostanoid DP receptor expressed in human H... 24900313
Prostaglandin D2 receptor IC50 = 280.0 nM 6.55 Displacement of [3H]PGD2 from human DP receptor expressed in HEK293 cells by sci... 22264478
ATP-binding cassette sub-family C member 3 IC50 = 1100.0 nM 5.96 Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... 23956101
Bile salt export pump IC50 = 11500.0 nM 4.94 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3301361 ADMET 6
19804971 10.1016/j.bmcl.2009.09.052 Rattus norvegicus 4
19804971 10.1016/j.bmcl.2009.09.052 Canis familiaris 4
19804971 10.1016/j.bmcl.2009.09.052 Cynomolgus monkey 4
24900313 10.1021/ml1002234 ADMET 4
24900313 10.1021/ml1002234 Prostaglandin D2 receptor 2 4
23956101 10.1093/toxsci/kft176 Unchecked 3
22119474 10.1016/j.bmcl.2011.10.123 Prostaglandin D2 receptor 2 3
22119474 10.1016/j.bmcl.2011.10.123 Prostaglandin D2 receptor 3
19804971 10.1016/j.bmcl.2009.09.052 Prostaglandin D2 receptor 2
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 2
24900313 10.1021/ml1002234 Prostaglandin D2 receptor 2
22264478 10.1016/j.bmcl.2011.12.107 Prostaglandin D2 receptor 2
22264478 10.1016/j.bmcl.2011.12.107 Prostaglandin D2 receptor 2 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
19804971 10.1016/j.bmcl.2009.09.052 Prostaglandin D2 receptor 2 2
19804971 10.1016/j.bmcl.2009.09.052 Prostaglandin E2 receptor EP4 subtype 1
19804971 10.1016/j.bmcl.2009.09.052 Thromboxane A2 receptor 1
24900313 10.1021/ml1002234 Cavia porcellus 1
19804971 10.1016/j.bmcl.2009.09.052 Unchecked 1

Data from ChEMBL 36 via Core Engine