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Compound Detail

CHEMBL3814206

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CC(C)[C@@H]1CN(c2ccc(CO)c(S(C)(=O)=O)c2)CCN1c1ncc(CO)c(C(F)(F)F)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3814206
Phase Preclinical
Structure Type MOL
InChI Key FPVIRRAMNBCEDK-KRWDZBQOSA-N
5
Targets
19
Activities
3
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

488.5
MW (Da)
2.23
ALogP
8
HBA
2
HBD
106.9
PSA (Ų)
0.64
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H27F3N4O4S
MW 488.53
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness -0.95

Activity Summary

Ki 7 meas. best 8.89
EC50 6 meas. best 8.4
IC50 6 meas. best 6.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Oxysterols receptor LXR-beta
CHEMBL4093
 Ki 8.89 8.6125 1.3 4
Liver X receptor
CHEMBL3706564
 EC50 8.4 8.31 4.0 2
Oxysterols receptor LXR-beta
CHEMBL4093
 EC50 7.68 7.68 21.0 2
Oxysterols receptor LXR-alpha
CHEMBL2808
 Ki 7.09 7.09 81.0 3
Oxysterols receptor LXR-alpha
CHEMBL2808
 EC50 6.61 6.61 244.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.22 6.03 608.0 3
Cytochrome P450 3A4
CHEMBL340
 IC50 5.18 4.7467 6600.0 3

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.7167 hr Homo sapiens
T1/2 1.167 hr Rattus norvegicus
T1/2 0.6667 hr Mus musculus
T1/2 0.1667 hr Macaca fascicularis
T1/2 0.7167 hr Homo sapiens
T1/2 1.15 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Oxysterols receptor LXR-beta Ki = 1.3 nM 8.89 Binding affinity to recombinant human LXRbeta-LBD expressed in Escherichia coli ... 31202993
Oxysterols receptor LXR-beta Ki = 3.0 nM 8.52 LXR alpha/beta Radioligand Binding Assay: Compounds of the invention were assess... -
Oxysterols receptor LXR-beta Ki = 3.0 nM 8.52 Displacement of radiolabeled T0901317 from LXRbeta LBD (unknown origin) 27599745
Oxysterols receptor LXR-beta Ki = 3.0 nM 8.52 Displacement of [3H]TO901317 from LXRbeta ligand binding domain (unknown origin)... 26990539
Liver X receptor EC50 = 4.0 nM 8.4 Agonist activity at LXR in human THP1 cells assessed as upregulation of ABCA1 ge... 26990539
Liver X receptor EC50 = 6.0 nM 8.22 Agonist activity at LXR in human HepG2 cells assessed as upregulation of SREBP1C... 26990539
Oxysterols receptor LXR-beta EC50 = 21.0 nM 7.68 Agonist activity at human LXRbeta ligand binding domain(155 to 460 residues) tra... 26990539
Oxysterols receptor LXR-beta EC50 = 21.0 nM 7.68 Agonist activity at LXRbeta LBD (unknown origin) fused with Gal4-DNA binding dom... 27599745
Oxysterols receptor LXR-alpha Ki = 81.0 nM 7.09 LXR alpha/beta Radioligand Binding Assay: Compounds of the invention were assess... -
Oxysterols receptor LXR-alpha Ki = 81.0 nM 7.09 Displacement of radiolabeled T0901317 from LXRalpha LBD (unknown origin) 27599745
Oxysterols receptor LXR-alpha Ki = 81.0 nM 7.09 Displacement of [3H]TO901317 from LXRalpha ligand binding domain (unknown origin... 26990539
Oxysterols receptor LXR-alpha EC50 = 244.0 nM 6.61 Agonist activity at LXRalpha LBD (unknown origin) fused with Gal4-DNA binding do... 27599745
Oxysterols receptor LXR-alpha EC50 = 244.0 nM 6.61 Agonist activity at human LXRalpha ligand binding domain(167 to 447 residues) tr... 26990539
Cytochrome P450 2C9 IC50 = 608.0 nM 6.22 Inhibition of CYP2C9 (unknown origin) 27599745
Cytochrome P450 2C9 IC50 = 610.0 nM 6.21 Inhibition of recombinant CYP2C9 (unknown origin) 26990539
Cytochrome P450 2C9 IC50 = 2200.0 nM 5.66 Inhibition of CYP2C9 in human liver microsomes 26990539
Cytochrome P450 3A4 IC50 = 6600.0 nM 5.18 Inhibition of CYP3A4 in human liver microsomes 26990539
Cytochrome P450 3A4 IC50 = 29450.0 nM 4.53 Inhibition of CYP3A4 (unknown origin) 27599745
Cytochrome P450 3A4 IC50 = 29430.0 nM 4.53 Inhibition of recombinant CYP3A4 (unknown origin) 26990539

Literature References

PubMed DOI Target Context # Activities
26990539 10.1021/acs.jmedchem.5b02029 Liver X receptor 20
26990539 10.1021/acs.jmedchem.5b02029 Oxysterols receptor LXR-beta 3
26990539 10.1021/acs.jmedchem.5b02029 Oxysterols receptor LXR-alpha 3
27599745 10.1016/j.bmcl.2016.08.089 Oxysterols receptor LXR-beta 3
27599745 10.1016/j.bmcl.2016.08.089 Oxysterols receptor LXR-alpha 3
26990539 10.1021/acs.jmedchem.5b02029 Liver microsome 2
27599745 10.1016/j.bmcl.2016.08.089 ADMET 2
26990539 10.1021/acs.jmedchem.5b02029 Cytochrome P450 2C9 2
26990539 10.1021/acs.jmedchem.5b02029 Cytochrome P450 2D6 2
26990539 10.1021/acs.jmedchem.5b02029 Cytochrome P450 3A4 2
31202993 10.1016/j.ejmech.2019.06.011 Oxysterols receptor LXR-beta 1
27599745 10.1016/j.bmcl.2016.08.089 Cytochrome P450 2C9 1
27599745 10.1016/j.bmcl.2016.08.089 Cytochrome P450 2D6 1
27599745 10.1016/j.bmcl.2016.08.089 Cytochrome P450 3A4 1
26990539 10.1021/acs.jmedchem.5b02029 Cynomolgus monkey 1
26990539 10.1021/acs.jmedchem.5b02029 Nuclear receptor subfamily 1 group I member 2 1
26990539 10.1021/acs.jmedchem.5b02029 Nuclear receptor ROR-alpha 1
26990539 10.1021/acs.jmedchem.5b02029 Retinoid X receptor 1
26990539 10.1021/acs.jmedchem.5b02029 Mineralocorticoid receptor 1
26990539 10.1021/acs.jmedchem.5b02029 ADMET 1

Data from ChEMBL 36 via Core Engine