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Compound Detail

CHEMBL12980

QUINUCLIDINYL BENZILATE
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O=C(OC1CN2CCC1CC2)C(O)(c1ccccc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL12980
Name QUINUCLIDINYL BENZILATE
Phase Preclinical
Structure Type MOL
InChI Key HGMITUYOCPPQLE-UHFFFAOYSA-N
11
Targets
18
Activities
4
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

337.4
MW (Da)
2.56
ALogP
4
HBA
1
HBD
49.8
PSA (Ų)
0.87
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H23NO3
MW 337.42
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 0.20

Activity Summary

Ki 14 meas. best 10.35
EC50 2 meas. best 5.37
IC50 1 meas. best 7.68
Kd 1 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor
CHEMBL2094109
 Ki 10.35 9.932 0.0 5
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 10.35 10.35 0.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
 Ki 10.29 10.29 0.1 1
Muscarinic acetylcholine receptor M2
CHEMBL309
 Ki 9.74 9.74 0.2 1
Muscarinic acetylcholine receptor M1
CHEMBL2672
 Ki 9.66 9.66 0.2 1
Muscarinic acetylcholine receptor M3
CHEMBL5498
 Ki 9.62 8.975 0.2 2
Muscarinic acetylcholine receptor DM1
CHEMBL2366467
 Ki 9.3 9.3 0.5 2
Cavia porcellus
CHEMBL369
 Kd 8.7 8.7 2.0 1
Rattus norvegicus
CHEMBL376
 IC50 7.68 7.68 21.0 1
Vesicular acetylcholine transporter
CHEMBL2125
 Ki 6.24 6.24 581.7 1
Trypanosoma cruzi
CHEMBL368
 EC50 5.37 5.33 4300.0 2

Pharmacokinetic Data

Parameter Value Units Species
KA 5280000000.0 M-1 Canis lupus familiaris
KA 4.5 M-1 -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor Ki = 0.045 nM 10.35 Ability of compound to displace (-)-[3H]3-Quinuclidinyl benzilate (-)-[3H]-QNB f... 9371246
Muscarinic acetylcholine receptor M2 Ki = 0.045 nM 10.35 Binding affinity for muscarinic acetylcholine receptor M2 by measuring displacem... 7853341
Muscarinic acetylcholine receptor Ki = 0.051 nM 10.29 Ability of compound to displace (-)-[3H]3-Quinuclidinyl benzilate (-)-[3H]-QNB f... 9371246
Muscarinic acetylcholine receptor M1 Ki = 0.051 nM 10.29 Binding affinity for muscarinic acetylcholine receptor M1 by measuring displacem... 7853341
Muscarinic acetylcholine receptor M2 Ki = 0.18 nM 9.74 In vitro binding affinity against rat heart membrane using [3H]-AF-DX-384 7752195
Muscarinic acetylcholine receptor Ki = 0.2 nM 9.7 Affinity for Muscarinic acetylcholine receptors in urinary bladder from Guinea P... 9371246
Muscarinic acetylcholine receptor Ki = 0.2 nM 9.7 Binding affinity for muscarinic acetylcholine receptor by measuring displacement... 7853341
Muscarinic acetylcholine receptor M1 Ki = 0.22 nM 9.66 In vitro binding affinity against bovine striatal membrane using [3H]pirenzepine 7752195
Muscarinic acetylcholine receptor Ki = 0.24 nM 9.62 Ability of compound to displace (-)-[3H]3-Quinuclidinyl benzilate (-)-[3H]-QNB f... 9371246
Muscarinic acetylcholine receptor M3 Ki = 0.24 nM 9.62 Binding affinity for muscarinic acetylcholine receptor M3 by measuring displacem... 7853341
Muscarinic acetylcholine receptor DM1 Ki = 0.5 nM 9.3 Displacement of [3H]QNB from Drosophila melanogaster mAChR by scintillation coun... 17319687
Muscarinic acetylcholine receptor DM1 Ki = 0.5 nM 9.3 Displacement of [3H]AF-DX 384 from Drosophila melanogaster mAChR by scintillatio... 17319687
Cavia porcellus Kd = 1.995 nM 8.7 Antimuscarinic activity was assayed for its ability to block the acetyl-choline ... 3494849
Muscarinic acetylcholine receptor M3 Ki = 4.63 nM 8.33 In vitro binding affinity against guinea pig ileum using [3H]N-methylscopolamine 7752195
Rattus norvegicus IC50 = 21.0 nM 7.68 Inhibition of carbachol-induced release of alpha-amylase from pancreatic acini f... 3494849
Vesicular acetylcholine transporter Ki = 581.7 nM 6.24 Displacement of [125I]O-iodo-trans-decalinvesamicol from VAChT in Sprague-Dawley... 22831799
Trypanosoma cruzi EC50 = 4300.0 nM 5.37 Trypanocidal activity against Trypanosoma cruzi Tulahuen LacZ intracellular amas... 34095840
Trypanosoma cruzi EC50 = 5100.0 nM 5.29 Trypanocidal activity against Trypanosoma cruzi Y intracellular amastigote form ... 34095840

Literature References

PubMed DOI Target Context # Activities
592326 10.1021/jm00222a015 Mus musculus 13
7562924 10.1021/jm00020a004 Rattus norvegicus 5
9371246 10.1021/jm970346t Muscarinic acetylcholine receptor 4
6644747 10.1021/jm00366a023 Mus musculus 3
34095840 10.1039/d0md00097c Unchecked 2
7131491 10.1021/jm00351a020 Muscarinic acetylcholine receptor 2
34095840 10.1039/d0md00097c Trypanosoma cruzi 2
17319687 10.1021/jf0631934 Muscarinic acetylcholine receptor DM1 2
1920351 10.1021/jm00114a006 Muscarinic acetylcholine receptor 2
3494849 10.1021/jm00388a010 Cavia porcellus 2
7853341 10.1021/jm00003a011 Muscarinic acetylcholine receptor 2
3494849 10.1021/jm00388a010 Rattus norvegicus 1
7853341 10.1021/jm00003a011 Muscarinic acetylcholine receptor M3 1
1920351 10.1021/jm00114a006 No relevant target 1
7853341 10.1021/jm00003a011 Muscarinic acetylcholine receptor M2 1
22831799 10.1016/j.bmc.2012.06.040 Vesicular acetylcholine transporter 1
7853341 10.1021/jm00003a011 Muscarinic acetylcholine receptor M1 1
7752195 10.1021/jm00010a016 Muscarinic acetylcholine receptor M3 1
- 10.6019/CHEMBL3301361 No relevant target 1
7752195 10.1021/jm00010a016 Muscarinic acetylcholine receptor M2 1

Data from ChEMBL 36 via Core Engine