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Compound Detail

CHEMBL111659

ALTINICLINE
🧪 Phase II
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🧪 Phase II
C#Cc1cncc([C@@H]2CCCN2C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL111659
Name ALTINICLINE
Phase Phase II
Structure Type MOL
InChI Key NUPUDYKEEJNZRG-LBPRGKRZSA-N

Known Names

(-)-5-ethynylnicotine Altiniclina Altinicline SIB-1508Y SIB-1765F
9
Targets
18
Activities
2
Assay Types
0
PK Parameters
18
Publications
5
Known Names
1
Mechanisms

Molecular Properties

186.3
MW (Da)
1.83
ALogP
2
HBA
0
HBD
16.1
PSA (Ų)
0.62
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -nicline
USAN Year 1999

Extended Properties

Molecular Formula C12H14N2
MW 186.26
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -0.47

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Neuronal acetylcholine receptor; alpha4/beta2 agonist AGONIST Neuronal acetylcholine receptor; alpha4/beta2 ✓ ✓

Activity Summary

EC50 16 meas. best 6.5
IC50 2 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal nicotinic acetylcholine receptor
CHEMBL3350222
 IC50 8.52 8.52 3.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 EC50 6.5 5.5775 320.0 4
Unchecked
CHEMBL612545
 EC50 6.43 6.43 370.0 1
Neuronal acetylcholine receptor; alpha4/beta4
CHEMBL1907591
 EC50 5.7 5.11 2000.0 3
Neuronal acetylcholine receptor; alpha2/beta4
CHEMBL2109230
 EC50 5.5 5.5 3200.0 1
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL2109234
 EC50 5.5 5.5 3200.0 1
Nicotinic acetylcholine receptor alpha2/beta4
CHEMBL3038459
 EC50 5.3 4.805 5000.0 2
Muscarinic acetylcholine receptor
CHEMBL1907609
 IC50 5.05 5.05 8900.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
 EC50 5.0 4.64 10000.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal nicotinic acetylcholine receptor IC50 = 3.0 nM 8.52 Binding affinity at NAChRs was determined by measuring the displacement of ([3H]... 8765504
Neuronal acetylcholine receptor; alpha4/beta2 EC50 = 320.0 nM 6.5 Effective concentration against Nicotinic acetylcholine receptor alpha4-beta2 16033252
Unchecked EC50 = 370.0 nM 6.43 functional assay: Nematode eggs are isolated from fresh feces by centrifugation ... -
Neuronal acetylcholine receptor; alpha4/beta2 EC50 = 1800.0 nM 5.75 The compound was tested on recombinant human alpha4-beta2 cell lines of Human em... 8765504
Neuronal acetylcholine receptor; alpha4/beta2 EC50 = 1800.0 nM 5.75 Partial agonist activity at alpha4beta2 nAChR (unknown origin) 24901260
Neuronal acetylcholine receptor; alpha4/beta4 EC50 = 2000.0 nM 5.7 Effective concentration against Nicotinic acetylcholine receptor alpha4-beta4 16033252
Neuronal acetylcholine receptor; alpha3/beta2 EC50 = 3200.0 nM 5.5 Effective concentration against Nicotinic acetylcholine receptor alpha3-beta2 16033252
Neuronal acetylcholine receptor; alpha2/beta4 EC50 = 3200.0 nM 5.5 Effective concentration against Nicotinic acetylcholine receptor alpha2-beta4 16033252
Nicotinic acetylcholine receptor alpha2/beta4 EC50 = 5000.0 nM 5.3 The compound was tested on recombinant human alpha2-beta4 cell lines of Human em... 8765504
Muscarinic acetylcholine receptor IC50 = 8900.0 nM 5.05 Muscarinic acetylcholine receptor binding (rat cortical membranes) was determine... 8765504
Neuronal acetylcholine receptor; alpha4/beta4 EC50 = 9000.0 nM 5.05 The compound was tested on recombinant human alpha4-beta4 cell lines of Human em... 8765504
Neuronal acetylcholine receptor; alpha3/beta4 EC50 = 10000.0 nM 5.0 Effective concentration against Nicotinic acetylcholine receptor alpha3-beta4 16033252
Neuronal acetylcholine receptor; alpha3/beta4 EC50 = 23000.0 nM 4.64 The compound was tested on recombinant human alpha3-beta4 cell lines of Human em... 8765504
Neuronal acetylcholine receptor; alpha3/beta4 EC50 = 23000.0 nM 4.64 Partial agonist activity at alpha3beta4 nAChR (unknown origin) 24901260
Neuronal acetylcholine receptor; alpha4/beta4 EC50 = 26000.0 nM 4.58 The compound was tested on recombinant human alpha4-beta4 cell lines of Human em... 8765504
Nicotinic acetylcholine receptor alpha2/beta4 EC50 = 49000.0 nM 4.31 The compound was tested on recombinant human alpha2-beta4 cell lines of Human em... 8765504
Neuronal acetylcholine receptor; alpha4/beta2 EC50 = 49000.0 nM 4.31 The compound was tested on recombinant human alpha4-beta2 cell lines of Human em... 8765504
Neuronal acetylcholine receptor; alpha3/beta4 EC50 = 52000.0 nM 4.28 The compound was tested on recombinant human alpha3-beta4 cell lines of Human em... 8765504

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
8765504 10.1021/jm960328w Nicotinic acetylcholine receptor alpha2/beta4 2
8765504 10.1021/jm960328w Neuronal acetylcholine receptor; alpha3/beta4 2
8765504 10.1021/jm960328w Neuronal acetylcholine receptor; alpha4/beta4 2
8765504 10.1021/jm960328w Neuronal acetylcholine receptor; alpha4/beta2 2
8765504 10.1021/jm960328w Acetylcholine receptor; alpha1/beta1/delta/gamma 2
24901260 10.1021/jm401937a Neuronal acetylcholine receptor; alpha4/beta2 2
24901260 10.1021/jm401937a Neuronal acetylcholine receptor; alpha3/beta4 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta2 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha2/beta4 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha3/beta4 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta4 2
16033252 10.1021/jm040219e Neuronal acetylcholine receptor subunit alpha-7 1
8765504 10.1021/jm960328w Neuronal nicotinic acetylcholine receptor 1
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha3/beta2 1
8765504 10.1021/jm960328w Rattus norvegicus 1
8765504 10.1021/jm960328w Muscarinic acetylcholine receptor 1

Data from ChEMBL 36 via Core Engine