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Compound Detail

CHEMBL3629569

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OC(CC1c2ccccc2-c2cncn21)C1CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3629569
Phase Preclinical
Structure Type MOL
InChI Key YTRRAUACYORZLX-UHFFFAOYSA-N
6
Targets
25
Activities
4
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

282.4
MW (Da)
3.78
ALogP
3
HBA
1
HBD
38.0
PSA (Ų)
0.93
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H22N2O
MW 282.39
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.26

Activity Summary

IC50 18 meas. best 7.55
EC50 4 meas. best 7.21
Ki 2 meas. best 8.15
Kd 1 meas. best 5.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 8.15 8.145 7.0 2
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 7.55 7.0 28.0 11
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 7.52 6.88 30.0 3
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 EC50 7.21 7.1325 61.0 4
Cytochrome P450 3A4
CHEMBL340
 IC50 6.77 6.77 170.0 1
Unchecked
CHEMBL612545
 IC50 6.4 6.4 398.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.66 5.66 2200.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Kd 5.48 5.48 3300.0 1
Cytochrome P450 2B6
CHEMBL4729
 IC50 5.23 5.23 5900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 18.03 mL.min-1.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Indoleamine 2,3-dioxygenase 1 Ki = 7.0 nM 8.15 Inhibition of IDO1 (unknown origin) 30108849
Indoleamine 2,3-dioxygenase 1 Ki = 7.2 nM 8.14 Inhibition of IDO1 (unknown origin) by in-vitro assay 28963992
Indoleamine 2,3-dioxygenase 1 IC50 = 28.0 nM 7.55 Inhibition of IDO1 (unknown origin) -
Tryptophan 2,3-dioxygenase IC50 = 30.0 nM 7.52 Inhibition of recombinant human TDO2 expressed in Escherichia coli BL21 (DE3) as... 33901770
Indoleamine 2,3-dioxygenase 1 IC50 = 38.0 nM 7.42 Inhibition of recombinant human IDO1 assessed as conversion of N-formylkynurenin... 26642377
Indoleamine 2,3-dioxygenase 1 IC50 = 50.0 nM 7.3 Inhibition of recombinant human IDO1 assessed as reduction in N-formylkynurenine... 33901770
Indoleamine 2,3-dioxygenase 1 IC50 = 60.0 nM 7.22 Inhibition of recombinant human IDO1 expressed in bacterial expression system us... 28011425
Indoleamine 2,3-dioxygenase 1 IC50 = 60.0 nM 7.22 Inhibition of purified human IDO1 using L-tryptophan as substrate preincubated f... 31264862
Indoleamine 2,3-dioxygenase 1 EC50 = 61.0 nM 7.21 Inhibition of IDO1 in IFNgamma-stimulated human HeLa cells incubated for 24 hrs 26642377
Indoleamine 2,3-dioxygenase 1 EC50 = 75.0 nM 7.12 Inhibition of IDO1 (unknown origin) by cell based assay 28963992
Indoleamine 2,3-dioxygenase 1 EC50 = 75.0 nM 7.12 Inhibition of IDO1 (unknown origin) by cell based assay 30108849
Indoleamine 2,3-dioxygenase 1 IC50 = 80.0 nM 7.1 Inhibition of recombinant human IDO1 expressed in Escherichia coli EC538 assesse... 33901770
Indoleamine 2,3-dioxygenase 1 EC50 = 83.0 nM 7.08 Inhibition of recombinant human IDO1 expressed in T-REx-293 cells assessed as re... 31264862
Indoleamine 2,3-dioxygenase 1 IC50 = 110.0 nM 6.96 Inhibition of recombinant human IDO1 expressed in Escherichia coli EC538 assesse... 33901770
Indoleamine 2,3-dioxygenase 1 IC50 = 130.0 nM 6.89 Inhibition of recombinant human IDO1 S167A mutant expressed in Escherichia coli ... 28011425
Tryptophan 2,3-dioxygenase IC50 = 150.0 nM 6.82 Inhibition of recombinant human TDO2 expressed in Escherichia coli BL21 (DE3) as... 33901770
Cytochrome P450 3A4 IC50 = 170.0 nM 6.77 Inhibition of CYP3A4 (unknown origin) using midazolam as substrate 31264862
Indoleamine 2,3-dioxygenase 1 IC50 = 190.0 nM 6.72 Inhibition of IDO1 in IFN-gamma stimulated human HeLa cells assessed as reductio... 31610376
Unchecked IC50 = 398.0 nM 6.4 IDO Coupled Biochemical Assays: In two separate assays, 0.045 μg/μl of human IDO... -
Indoleamine 2,3-dioxygenase 1 IC50 = 410.0 nM 6.39 Inhibition of IFNgamma-induced IDO1 in human HeLa cells using L-tryptophan as su... 28667875

Literature References

PubMed DOI Target Context # Activities
28963992 10.1016/j.ejmech.2017.09.025 Indoleamine 2,3-dioxygenase 1 5
28011425 10.1016/j.ejmech.2016.12.029 Indoleamine 2,3-dioxygenase 1 5
26642377 10.1021/acs.jmedchem.5b01390 Indoleamine 2,3-dioxygenase 1 3
33901770 10.1016/j.bmc.2021.116160 Indoleamine 2,3-dioxygenase 1 3
28667875 10.1016/j.ejmech.2017.06.039 Indoleamine 2,3-dioxygenase 1 3
29031064 10.1016/j.ejmech.2017.09.044 Indoleamine 2,3-dioxygenase 1 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
31610376 10.1016/j.ejmech.2019.111750 Indoleamine 2,3-dioxygenase 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
33901770 10.1016/j.bmc.2021.116160 Tryptophan 2,3-dioxygenase 2
31264862 10.1021/acs.jmedchem.9b00662 Indoleamine 2,3-dioxygenase 1 2
30108849 10.1039/C7MD00109F Indoleamine 2,3-dioxygenase 1 2
29031064 10.1016/j.ejmech.2017.09.044 No relevant target 2
- 10.1039/C5MD00317B Indoleamine 2,3-dioxygenase 1 2
26642377 10.1021/acs.jmedchem.5b01390 Mus musculus 2
26207924 10.1021/acs.jmedchem.5b00461 Indoleamine 2,3-dioxygenase 1 1
28963992 10.1016/j.ejmech.2017.09.025 HeLa 1
26642377 10.1021/acs.jmedchem.5b01390 Canis familiaris 1
26642377 10.1021/acs.jmedchem.5b01390 Rattus norvegicus 1
25970480 10.1021/acs.jmedchem.5b00326 Indoleamine 2,3-dioxygenase 1 1

Data from ChEMBL 36 via Core Engine