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Compound Detail

CHEMBL14145

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c1ccc(-c2c[nH]cn2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL14145
Phase Preclinical
Structure Type MOL
InChI Key XHLKOHSAWQPOFO-UHFFFAOYSA-N
7
Targets
32
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

144.2
MW (Da)
2.08
ALogP
1
HBA
1
HBD
28.7
PSA (Ų)
0.65
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C9H8N2
MW 144.18
Aromatic Rings 2
Heavy Atoms 11
NP-Likeness -0.62

Activity Summary

IC50 27 meas. best 6.57
Ki 3 meas. best 5.36
Kd 2 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.57 5.445 270.0 2
ADMET
CHEMBL612558
 Kd 6.52 6.52 300.0 1
Sterol 14alpha-demethylase
CHEMBL5090
 Kd 5.89 5.89 1300.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.82 5.025 1500.0 4
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 5.36 5.36 4400.0 1
Cytochrome P450 2B1
CHEMBL3335
 IC50 5.13 5.13 7400.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 4.7 4.3938 20000.0 16
Unchecked
CHEMBL612545
 Ki 4.7 4.64 20000.0 2
Cytochrome P450 1A1
CHEMBL2922
 IC50 4.48 4.48 33000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 270.0 nM 6.57 Inhibition of IMPDH (unknown origin) 32259446
ADMET Kd = 300.0 nM 6.52 Binding affinity to C-terminal His4-tagged CYP2B4 dH/H226Y mutant (unknown origi... 21502194
Sterol 14alpha-demethylase Kd = 1300.0 nM 5.89 Binding affinity to Mycobacterium tuberculosis His4-tagged recombinant CYP51 sub... 17846131
Cytochrome P450 3A4 IC50 = 1500.0 nM 5.82 null: A commercially available P450-GLO Assay kit (Promega Corporation, Madison ... -
Cytochrome P450 3A4 IC50 = 1500.0 nM 5.82 In vitro CYP3A4 Inhibition Assay: Cytochrome P450 is a large and diverse group o... -
Indoleamine 2,3-dioxygenase 1 Ki = 4400.0 nM 5.36 Inhibition of human recombinant indoleamine 2,3-dioxygenase by Eadie-Hofstee plo... 18665584
Cytochrome P450 2B1 IC50 = 7400.0 nM 5.13 Inhibition of Aminopyrine N-demethylase in Phenobarbitone-treated rats 7097715
Indoleamine 2,3-dioxygenase 1 IC50 = 20000.0 nM 4.7 Inhibition of full-length human IDO1 expressed in Escherichia coli Rosetta (DE3)... 31525930
Unchecked Ki = 20000.0 nM 4.7 Compound was evaluated for inhibition constant, in liver microsomes from 3-methy... 7277387
Indoleamine 2,3-dioxygenase 1 IC50 = 21000.0 nM 4.68 Inhibition of recombinant human IDO1 expressed in Escherichia coli Rosetta (DE3)... 33557523
Unchecked Ki = 26000.0 nM 4.58 Compound was evaluated for inhibition constant, in liver microsomes from beta-na... 7277387
Indoleamine 2,3-dioxygenase 1 IC50 = 27000.0 nM 4.57 Inhibition of purified human IDO1 using L-tryptophan as substrate preincubated f... 31264862
Indoleamine 2,3-dioxygenase 1 IC50 = 31000.0 nM 4.51 Inhibition of recombinant human IDO1 expressed in bacterial expression system us... 28011425
Cytochrome P450 1A1 IC50 = 33000.0 nM 4.48 Inhibition of Aryl hydrocarbon hydroxylase in phenobarbitone-treated rats 7097715
Indoleamine 2,3-dioxygenase 1 IC50 = 38000.0 nM 4.42 Inhibition of recombinant human IDO1 expressed in bacterial expression system us... 28011425
Indoleamine 2,3-dioxygenase 1 IC50 = 39000.0 nM 4.41 IDO Enzyme Inhibitory Activity: Firstly, the compound was subject to a 3-fold gr... -
Indoleamine 2,3-dioxygenase 1 IC50 = 42000.0 nM 4.38 Inhibition of recombinant human IDO1 expressed in bacterial expression system us... 28011425
Indoleamine 2,3-dioxygenase 1 IC50 = 48000.0 nM 4.32 Inhibition of human recombinant indoleamine 2,3-dioxygenase in presence of D-try... 18665584
Indoleamine 2,3-dioxygenase 1 IC50 = 48000.0 nM 4.32 Inhibition of human IDO1 using L-tryptophan as substrate assessed as reduction i... 37866714
Indoleamine 2,3-dioxygenase 1 IC50 = 48000.0 nM 4.32 Inhibition of IDO1 (unknown origin) 34752953

Literature References

PubMed DOI Target Context # Activities
7277387 10.1021/jm00139a011 NON-PROTEIN TARGET 12
31525930 10.1021/acs.jmedchem.9b00942 Indoleamine 2,3-dioxygenase 1 9
28011425 10.1016/j.ejmech.2016.12.029 Indoleamine 2,3-dioxygenase 1 9
7277387 10.1021/jm00139a011 Unchecked 4
4020834 10.1021/jm00146a028 Unchecked 3
7097715 10.1021/jm00348a003 Cytochrome P450 1A1 3
7097715 10.1021/jm00348a003 Cytochrome P450 2B1 2
18665584 10.1021/jm800512z Indoleamine 2,3-dioxygenase 1 2
33557523 10.1021/acs.jmedchem.0c01968 Indoleamine 2,3-dioxygenase 1 2
22616902 10.1021/jm300260v No relevant target 2
24262887 10.1016/j.bmc.2013.10.037 Indoleamine 2,3-dioxygenase 1 2
- 10.1039/C5MD00317B Indoleamine 2,3-dioxygenase 1 2
- 10.1039/C5MD00317B A-375 2
31525930 10.1021/acs.jmedchem.9b00942 No relevant target 2
36403421 10.1016/j.ejmech.2022.114935 Phosphoserine phosphatase SerB2 2
17846131 10.1128/aac.00311-07 Sterol 14alpha-demethylase 1
23521768 10.1021/jm400049z Indoleamine 2,3-dioxygenase 1 1
21502194 10.1124/dmd.111.039719 ADMET 1
26207924 10.1021/acs.jmedchem.5b00461 Indoleamine 2,3-dioxygenase 1 1
26599519 10.1021/acs.jmedchem.5b01616 Cytosolic purine 5'-nucleotidase 1

Data from ChEMBL 36 via Core Engine