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Compound Detail

CHEMBL510275

METHYLLYCACONITINE
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CCN1C[C@]2(COC(=O)c3ccccc3N3C(=O)C[C@H](C)C3=O)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@@H]5[C@](O)(C[C@@H]6OC)[C@](O)([C@@H](OC)[C@H]23)[C@@H]14

Basic Information

ChEMBL ID CHEMBL510275
Name METHYLLYCACONITINE
Phase Preclinical
Structure Type MOL
InChI Key XLTANAWLDBYGFU-BVFBBISOSA-N
7
Targets
63
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

682.8
MW (Da)
2.04
ALogP
11
HBA
2
HBD
144.3
PSA (Ų)
0.29
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C37H50N2O10
MW 682.81
Aromatic Rings 1
Heavy Atoms 49
NP-Likeness 2.64

Activity Summary

Ki 48 meas. best 9.82
IC50 14 meas. best 8.12
EC50 1 meas. best 4.53

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.82 8.3737 0.1 27
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
Ki 9.22 8.4144 0.6 9
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
Ki 9.0 8.5857 1.0 7
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL1907587
Ki 8.64 8.64 2.3 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
IC50 8.12 8.12 7.6 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
IC50 8.08 8.08 8.3 4
Unchecked
CHEMBL612545
IC50 7.05 5.7538 89.0 8
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
Ki 6.4 6.0167 400.0 3
Neuronal acetylcholine receptor subunit alpha-10
CHEMBL3461
Ki 5.89 5.89 1300.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
IC50 5.58 5.58 2600.0 1
Unchecked
CHEMBL612545
EC50 4.53 4.53 29512.1 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.15 nM 9.82 Displacement of [3H]IMD from nAChR in Myzus persicae 4106A (green peach aphid) m... 23112103
Unchecked Ki = 0.37 nM 9.43 Displacement of [3H]-methyl-SFX from nAChR in Myzus persicae 4106A (green peach ... 23112103
Neuronal acetylcholine receptor subunit alpha-7 Ki = 0.6 nM 9.22 Binding affinity against alpha7 nAChR (nicotinic acetylcholine receptor) using [... 10649969
Neuronal acetylcholine receptor subunit alpha-7 Ki = 0.8 nM 9.1 Binding affinity against alpha-7 nAChR (nicotinic acetylcholine receptor) using ... 10649969
Neuronal acetylcholine receptor subunit alpha-7 Ki = 0.87 nM 9.06 Displacement of [125I]iodoMLA from alpha-7 nAChR in rat cerebral cortex 17098430
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.0 nM 9.0 Displacement of [3H]methyllycaconitine from human alpha-7 in tsA201 cells coexpr... 17722904
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.1 nM 8.96 Displacement of [3H]methyllycaconitine from human alpha-7 in tsA201 cells coexpr... 17722904
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.6 nM 8.8 Displacement of [3H]methyllycaconitine from chimeric alpha7nAChR/5HT3A in tsA201... 17722904
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.622 nM 8.79 Displacement of [3H]methyllycaconitine from chimeric alpha7nAChR/5HT3A in tsA201... 17722904
Unchecked Ki = 1.66 nM 8.78 Displacement of [3H]methyllycaconitine from chimeric alpha-7nAChR Y195F mutant/5... 17722904
Unchecked Ki = 1.7 nM 8.77 Displacement of [3H]methyllycaconitine from chimeric alpha-7nAChR Y195F mutant/5... 17722904
Unchecked Ki = 1.9 nM 8.72 Displacement of [3H]methyllycaconitine from chimeric alpha-7nAChR Y168A mutant/5... 17722904
Unchecked Ki = 1.95 nM 8.71 Displacement of [3H]methyllycaconitine from chimeric alpha-7nAChR Y168A mutant/5... 17722904
Neuronal acetylcholine receptor; alpha3/beta2 Ki = 2.3 nM 8.64 Affinity for Nicotinic acetylcholine receptor alpha4-beta2 tested by analogue-in... 11354387
Neuronal acetylcholine receptor subunit alpha-7 Ki = 2.3 nM 8.64 Binding affinity nicotinic acetylcholine receptor alpha-7 was evaluated by its a... 12372503
Neuronal acetylcholine receptor subunit alpha-7 Ki = 2.3 nM 8.64 Inhibitory constant against [3H]methyllycaconitine binding towards Nicotinic ace... 15808471
Unchecked Ki = 2.512 nM 8.6 Displacement of [3H]methyllycaconitine from chimeric alpha-7nAChR S148A mutant /... 17722904
Unchecked Ki = 2.5 nM 8.6 Displacement of [3H]methyllycaconitine from chimeric alpha-7nAChR S148A mutant /... 17722904
Neuronal acetylcholine receptor subunit alpha-7 Ki = 2.91 nM 8.54 Displacement of [125I]alpha-bungarotoxin from rat cortical membrane alpha7-nAChR... 24050653
Unchecked Ki = 3.2 nM 8.49 Displacement of [3H]methyllycaconitine from chimeric alpha-7nAChR N107A mutant/5... 17722904

Literature References

PubMed DOI Target Context # Activities
17722904 10.1021/jm070574f Unchecked 39
17722904 10.1021/jm070574f Neuronal acetylcholine receptor subunit alpha-7 10
20594622 10.1016/j.ejmech.2010.05.042 Unchecked 4
17098430 10.1016/j.bmc.2006.10.061 Mus musculus 3
10649969 10.1021/jm990544f Neuronal acetylcholine receptor subunit alpha-7 3
23112103 10.1002/ps.3413 Unchecked 2
17722904 10.1021/jm070574f Neuronal acetylcholine receptor; alpha3/beta4 2
17722904 10.1021/jm070574f 5-hydroxytryptamine receptor 3A 2
15203153 10.1016/j.bmcl.2004.05.001 Neuronal acetylcholine receptor subunit alpha-10 1
15808471 10.1016/j.bmcl.2005.02.045 Neuronal acetylcholine receptor subunit alpha-7 1
16033252 10.1021/jm040219e Neuronal acetylcholine receptor subunit alpha-7 1
24050653 10.1021/jm401184f Neuronal acetylcholine receptor subunit alpha-7 1
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta2 1
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha3/beta2 1
10465558 10.1016/s0960-894x(99)00378-9 Chromaffin cell neuronal nicotinic acetylcholine receptor 1
15050620 10.1016/j.bmcl.2004.01.004 Neuronal acetylcholine receptor subunit alpha-7 1
8941400 10.1021/jm9604991 Neuronal acetylcholine receptor subunit alpha-7 1
12467625 10.1016/s0960-894x(02)00849-1 Neuronal acetylcholine receptor subunit alpha-7 1
12372503 10.1016/s0960-894x(02)00687-x Neuronal acetylcholine receptor subunit alpha-7 1
12372503 10.1016/s0960-894x(02)00687-x Neuronal acetylcholine receptor; alpha4/beta2 1

Data from ChEMBL 36 via Core Engine