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Compound Detail

CHEMBL3959509

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O=C(O)C1CN(Cc2ccc3c(c2)CCc2c-3noc2-c2onc(-c3ccccc3)c2C(F)(F)F)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3959509
Phase Preclinical
Structure Type MOL
InChI Key IVRVCMWFTIBONM-UHFFFAOYSA-N
7
Targets
12
Activities
2
Assay Types
29
PK Parameters
14
Publications
0
Known Names

Molecular Properties

495.5
MW (Da)
5.30
ALogP
6
HBA
1
HBD
92.6
PSA (Ų)
0.40
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H20F3N3O4
MW 495.46
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -0.76

Activity Summary

EC50 7 meas. best 10.49
IC50 5 meas. best 9.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 EC50 10.49 8.9867 0.0 3
Sphingosine 1-phosphate receptor 1
CHEMBL1914263
 EC50 9.51 9.51 0.3 1
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 IC50 9.42 8.33 0.4 2
Rattus norvegicus
CHEMBL376
 EC50 8.6 8.11 2.5 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.7 5.7 2000.0 1
Sphingosine 1-phosphate receptor 3
CHEMBL3892
 EC50 5.36 5.36 4400.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.85 4.85 14000.0 1
Cytochrome P450 2C8
CHEMBL3721
 IC50 4.85 4.85 14000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 15012.44 ng.hr.mL-1 Mus musculus
AUC 743.19 ng.hr.mL-1 Rattus norvegicus
AUC 1684.56 ng.hr.mL-1 Macaca fascicularis
AUC 1238.65 ng.hr.mL-1 Canis lupus familiaris
CL 1.7 mL.min-1.kg-1 Mus musculus
CL 8.5 mL.min-1.kg-1 Rattus norvegicus
CL 2.4 mL.min-1.kg-1 Macaca fascicularis
CL 1.4 mL.min-1.kg-1 Canis lupus familiaris
Cmax 3600.0 nM Mus musculus
Cmax 140.0 nM Rattus norvegicus
Cmax 410.0 nM Macaca fascicularis
Cmax 90.0 nM Canis lupus familiaris
F 80.0 % Mus musculus
F 43.0 % Rattus norvegicus
F 80.0 % Macaca fascicularis
F 95.0 % Canis lupus familiaris
T1/2 2.0 hr Homo sapiens
T1/2 2.0 hr Mus musculus
T1/2 2.0 hr Rattus norvegicus
T1/2 2.0 hr Canis lupus familiaris
T1/2 2.0 hr Macaca mulatta
T1/2 15.0 hr Mus musculus
T1/2 7.9 hr Rattus norvegicus
T1/2 18.0 hr Macaca fascicularis
T1/2 23.1 hr Canis lupus familiaris
Tmax 3.0 hr Mus musculus
Tmax 4.0 hr Rattus norvegicus
Tmax 4.0 hr Macaca fascicularis
Tmax 8.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingosine 1-phosphate receptor 1 EC50 = 0.032 nM 10.49 Agonist activity at human S1P1 assessed as stimulation of cAMP accumulation 27726358
Sphingosine 1-phosphate receptor 1 EC50 = 0.31 nM 9.51 Agonist activity at rat S1P1 expressed in CHO cell membranes assessed as stimula... 27726358
Sphingosine 1-phosphate receptor 1 IC50 = 0.38 nM 9.42 Binding affinity to human S1P1 27726358
Sphingosine 1-phosphate receptor 1 EC50 = 0.59 nM 9.23 Agonist activity at human S1P1 expressed in CHO cell membranes assessed as stimu... 27726358
Rattus norvegicus EC50 = 2.5 nM 8.6 Reduction in circulating lymphocytes count in Lewis rat blood administered orall... 27726358
Rattus norvegicus EC50 = 24.0 nM 7.62 Antiarthritic activity in Lewis rat model of Complete Freund's adjuvant-induced ... 27726358
Sphingosine 1-phosphate receptor 1 EC50 = 57.0 nM 7.24 GTPgammaS Binding Assay: Compounds were loaded in a 384 Falcon v-bottom plate (0... -
Sphingosine 1-phosphate receptor 1 IC50 = 57.0 nM 7.24 Binding Assay: Membranes were prepared from CHO cells expressing human S1P1. Cel... -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 2000.0 nM 5.7 Inhibition of human ERG by patch clamp assay 27726358
Sphingosine 1-phosphate receptor 3 EC50 = 4400.0 nM 5.36 Agonist activity at human S1P3 expressed in CHO cell membranes assessed as stimu... 27726358
Cytochrome P450 3A4 IC50 = 14000.0 nM 4.85 Inhibition of CYP3A4 (unknown origin) using 7-benzyloxy resorufin as substrate 27726358
Cytochrome P450 2C8 IC50 = 14000.0 nM 4.85 Inhibition of CYP2C8 (unknown origin) 27726358

Literature References

PubMed DOI Target Context # Activities
27726358 10.1021/acs.jmedchem.6b01099 ADMET 43
27726358 10.1021/acs.jmedchem.6b01099 Rattus norvegicus 9
27726358 10.1021/acs.jmedchem.6b01099 Sphingosine 1-phosphate receptor 1 6
27726358 10.1021/acs.jmedchem.6b01099 Unchecked 6
27726358 10.1021/acs.jmedchem.6b01099 Sphingosine 1-phosphate receptor 3 1
27726358 10.1021/acs.jmedchem.6b01099 Voltage-gated inwardly rectifying potassium channel KCNH2 1
27726358 10.1021/acs.jmedchem.6b01099 Nuclear receptor subfamily 1 group I member 2 1
27726358 10.1021/acs.jmedchem.6b01099 Cytochrome P450 1A2 1
27726358 10.1021/acs.jmedchem.6b01099 Cytochrome P450 2B6 1
27726358 10.1021/acs.jmedchem.6b01099 Cytochrome P450 2C9 1
27726358 10.1021/acs.jmedchem.6b01099 Cytochrome P450 2C19 1
27726358 10.1021/acs.jmedchem.6b01099 Cytochrome P450 2D6 1
27726358 10.1021/acs.jmedchem.6b01099 Cytochrome P450 3A4 1
27726358 10.1021/acs.jmedchem.6b01099 Cytochrome P450 2C8 1

Data from ChEMBL 36 via Core Engine