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Compound Detail

CHEMBL27673

METHOCTRAMINE
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COc1ccccc1CNCCCCCCNCCCCCCCCNCCCCCCNCc1ccccc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL27673
Name METHOCTRAMINE
Phase Preclinical
Structure Type MOL
InChI Key RPMBYDYUVKEZJA-UHFFFAOYSA-N
16
Targets
57
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

582.9
MW (Da)
7.22
ALogP
6
HBA
4
HBD
66.6
PSA (Ų)
0.08
QED
2
Ro5 Violations
29
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C36H62N4O2
MW 582.92
Aromatic Rings 2
Heavy Atoms 42
NP-Likeness -0.21

Activity Summary

Ki 32 meas. best 8.62
IC50 11 meas. best 7.47
Kd 11 meas. best 7.92
EC50 3 meas. best 7.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 8.62 7.81 2.4 5
Muscarinic acetylcholine receptor M2
CHEMBL211
 Kd 7.92 7.836 12.0 5
Muscarinic acetylcholine receptor M2
CHEMBL309
 Ki 7.84 7.808 14.4 5
Unchecked
CHEMBL612545
 Ki 7.58 7.22 26.3 2
Muscarinic acetylcholine receptor M4
CHEMBL317
 Ki 7.58 7.55 26.3 3
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 7.47 7.3967 34.0 3
Muscarinic acetylcholine receptor M1
CHEMBL276
 Ki 7.43 7.4175 37.1 4
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Ki 7.42 7.195 38.0 2
Muscarinic acetylcholine receptor M1
CHEMBL216
 Ki 7.3 7.19 49.8 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.07 6.525 84.5 2
Glutamate NMDA receptor; GRIN1/GRIN2A
CHEMBL1907604
 IC50 6.86 6.86 138.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
 Kd 6.85 6.85 141.2 1
Muscarinic acetylcholine receptor M3
CHEMBL245
 Ki 6.56 6.42 277.0 2
Muscarinic acetylcholine receptor M5
CHEMBL2035
 Ki 6.5 6.38 313.0 2
Muscarinic acetylcholine receptor M3
CHEMBL5498
 Kd 6.44 6.244 363.1 5
Muscarinic acetylcholine receptor M3
CHEMBL320
 Ki 6.02 5.98 955.0 5
Cholinesterase
CHEMBL1914
 IC50 6.01 6.01 977.2 2
Unchecked
CHEMBL612545
 IC50 5.93 5.93 1174.9 2
Muscarinic acetylcholine receptor M2
CHEMBL4781
 EC50 5.52 5.52 2999.2 1
Acetylcholinesterase
CHEMBL220
 IC50 5.27 5.27 5370.3 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M2 Ki = 2.399 nM 8.62 Displacement of [3H] N-methyl-scopolamine chloride from human muscarinic recepto... 17276075
Muscarinic acetylcholine receptor M2 Kd = 12.02 nM 7.92 Antagonistic potency against Muscarinic acetylcholine receptor M2 9784091
Muscarinic acetylcholine receptor M2 Kd = 12.3 nM 7.91 Antagonist affinity evaluated against Muscarinic acetylcholine receptor M2 in is... 9767650
Muscarinic acetylcholine receptor M2 Ki = 14.3 nM 7.84 Affinity for human muscarinic acetylcholine receptor M2 expressed in CHO-K1 cell... 11708906
Muscarinic acetylcholine receptor M2 Ki = 14.45 nM 7.84 Inhibition of binding of [3H]N-methylscopolamine to muscarinic receptor (M2) in ... -
Muscarinic acetylcholine receptor M2 Ki = 14.45 nM 7.84 Tested for affinity constant against M2 muscarinic receptor rat heart using [3H]... 7932564
Muscarinic acetylcholine receptor M2 Ki = 14.45 nM 7.84 Affinity constant measured against M2 muscarinic receptor in rat heart 8246244
Muscarinic acetylcholine receptor M2 Ki = 15.0 nM 7.82 Compound was tested for its binding affinity towards Muscarinic acetylcholine re... 9572880
Muscarinic acetylcholine receptor M2 Kd = 15.14 nM 7.82 Antagonistic activity measured in isolated guinea pig left atrium (M2 receptor) 8246244
Muscarinic acetylcholine receptor M2 Kd = 15.14 nM 7.82 Antagonistic activity against M2 muscarinic receptor in guinea pig left atrium d... 7932564
Muscarinic acetylcholine receptor M2 Kd = 19.5 nM 7.71 Antagonist potency against carbachol induced inhibition of electrically stimulat... 2909747
Muscarinic acetylcholine receptor M2 Ki = 19.95 nM 7.7 Inhibition of [3H]NMS binding to rat heart Muscarinic acetylcholine receptor M2 9767650
Muscarinic acetylcholine receptor M4 Ki = 26.3 nM 7.58 Affinity constant measured against M4 muscarinic receptor rat NG108-15 cells 8246244
Unchecked Ki = 26.3 nM 7.58 Tested for affinity constant against M4 muscarinic receptor in NG 108-15 cell ho... 7932564
Muscarinic acetylcholine receptor M4 Ki = 26.3 nM 7.58 Inhibition of binding of [3H]N-methylscopolamine to Muscarinic acetylcholine rec... -
Muscarinic acetylcholine receptor M2 Ki = 26.0 nM 7.58 Binding affinity to human muscarinic M2 receptor by radioligand displacement ass... 23466604
Muscarinic acetylcholine receptor M2 Ki = 27.0 nM 7.57 Displacement of [3H]AF-DX384 from human recombinant M2 receptor expressed in CHO... 24805037
Muscarinic acetylcholine receptor M4 Ki = 32.36 nM 7.49 Inhibition of NG 108-15 binding to Muscarinic acetylcholine receptor M4 9767650
Muscarinic acetylcholine receptor M2 IC50 = 34.0 nM 7.47 Percent inhibition against Muscarinic acetylcholine receptor M2 at 1 uM 16250647
Muscarinic acetylcholine receptor M2 Ki = 36.0 nM 7.44 Displacement of radiolabeled methoctramine from human muscarinic M2 receptor 18983139

Literature References

PubMed DOI Target Context # Activities
17276075 10.1016/j.bmc.2007.01.022 Mus musculus 16
22243489 10.1021/jm2013216 Unchecked 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
12620072 10.1021/jm021055+ Muscarinic acetylcholine receptor M2 2
9767650 10.1021/jm981038d Muscarinic acetylcholine receptor M2 2
9767650 10.1021/jm981038d Muscarinic acetylcholine receptor M3 2
7932564 10.1021/jm00046a021 Muscarinic acetylcholine receptor M2 2
17276075 10.1016/j.bmc.2007.01.022 Muscarinic acetylcholine receptor M3 2
17276075 10.1016/j.bmc.2007.01.022 Muscarinic acetylcholine receptor M2 2
23466604 10.1016/j.ejmech.2013.01.044 Muscarinic acetylcholine receptor M2 2
8246244 10.1021/jm00075a032 Muscarinic acetylcholine receptors; M2 & M3 2
7932564 10.1021/jm00046a021 Muscarinic acetylcholine receptor M3 2
8246244 10.1021/jm00075a032 Muscarinic acetylcholine receptor M3 2
8246244 10.1021/jm00075a032 Muscarinic acetylcholine receptor M2 2
18983139 10.1021/jm8007618 Muscarinic acetylcholine receptor M2 2
31063379 10.1021/acs.jmedchem.8b01781 Escherichia coli 2
17417631 10.1038/nchembio873 NON-PROTEIN TARGET 2
17276075 10.1016/j.bmc.2007.01.022 Muscarinic acetylcholine receptor M4 2
8246244 10.1021/jm00075a032 Muscarinic acetylcholine receptor M4 1
38190615 10.1021/acs.jmedchem.3c02148 Muscarinic acetylcholine receptor M1 1

Data from ChEMBL 36 via Core Engine