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Compound Detail

CHEMBL1258006

BRADANICLINE
🧪 Phase II
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🧪 Phase II
O=C(N[C@@H]1C2CCN(CC2)[C@H]1Cc1cccnc1)c1cc2ccccc2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1258006
Name BRADANICLINE
Phase Phase II
Structure Type MOL
InChI Key OXKRFEWMSWPKKV-GHTZIAJQSA-N

Known Names

ATA-101 Bradaniclina Bradanicline TC 5619 TC-5619
7
Targets
15
Activities
4
Assay Types
2
PK Parameters
20
Publications
5
Known Names
3
Indications
1
Mechanisms

Molecular Properties

361.4
MW (Da)
3.26
ALogP
4
HBA
1
HBD
58.4
PSA (Ų)
0.77
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -nicline
USAN Year 2013

Extended Properties

Molecular Formula C22H23N3O2
MW 361.45
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.49

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Neuronal acetylcholine receptor protein alpha-7 subunit agonist AGONIST Neuronal acetylcholine receptor subunit alpha-7 ✓ ✓

Indications

Attention Deficit Disorder with Hyperactivity Cough Schizophrenia

Activity Summary

Ki 10 meas. best 9.38
EC50 2 meas. best 7.77
Kd 2 meas. best 7.7
IC50 1 meas. best 4.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 Ki 9.38 9.19 0.4 2
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 Ki 9.0 8.8533 1.0 3
Acetylcholine-binding protein
CHEMBL6084
 Ki 7.84 7.84 14.4 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
 EC50 7.77 7.77 17.0 1
Acetylcholine-binding protein
CHEMBL6084
 Kd 7.7 7.7 19.9 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
 EC50 7.48 7.48 33.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
 Ki 5.77 5.77 1700.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
 Ki 5.68 5.68 2100.0 1
Unchecked
CHEMBL612545
 Kd 5.29 5.29 5128.6 1
Unchecked
CHEMBL612545
 Ki 4.89 4.89 13000.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.27 4.27 54000.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 20.0 % Rattus norvegicus
T1/2 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor subunit alpha-7 Ki = 0.42 nM 9.38 Displacement of [3H]methyllycaconitine form alpha7 nAchR in rat hippocampal memb... 23126648
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.0 nM 9.0 Binding affinity to alpha7 nAChR in rat hippocampal membranes 21919481
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.0 nM 9.0 Binding affinity to human alpha7 nAChR expressed in HEK293 cells co-expressing R... 21919481
Neuronal acetylcholine receptor subunit alpha-7 Ki = 1.0 nM 9.0 Displacement of [3H]epibatidine form human alpha7 nAchR expressed in HEK293 cell... 23126648
Neuronal acetylcholine receptor subunit alpha-7 Ki = 2.754 nM 8.56 Displacement of [3H]-MLA from human alpha7 nAChR expressed in human SH-SY5Y cell... 20828128
Acetylcholine-binding protein Ki = 14.45 nM 7.84 Displacement of [3H]epibatidine from Lymnaea stagnalis His6-AChBP expressed in B... 20828128
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 17.0 nM 7.77 Agonist activity at rat alpha7 nAchR expressed in GH4C1 cells by whole cell patc... 23126648
Acetylcholine-binding protein Kd = 19.95 nM 7.7 Binding affinity to Lymnaea stagnalis His6-AChBP expressed in Bac-to-Bac baculov... 20828128
Neuronal acetylcholine receptor subunit alpha-7 EC50 = 33.0 nM 7.48 Agonist activity at human alpha7 nAChR expressed in Xenopus oocyte 21919481
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 1700.0 nM 5.77 Displacement of [3H]nicotine human alpha4beta2 nAChR in SH-EP1 cell membranes 23126648
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 2100.0 nM 5.68 Displacement of [3H]nicotine alpha4beta2 nAChR in rat cortical membranes 23126648
Unchecked Kd = 5128.61 nM 5.29 Binding affinity to Aplysia californica His6-AChBP expressed in Bac-to-Bac bacul... 20828128
Unchecked Ki = 13000.0 nM 4.89 Inhibition of non-selective opioid receptor 21919481
Unchecked Ki = 13000.0 nM 4.89 Inhibition of sodium channel site 2 21919481
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 54000.0 nM 4.27 Inhibition of human ERG expressed in CHO cells by whole cell voltage clamp assay 23126648

Literature References

PubMed DOI Target Context # Activities
21919481 10.1021/jm2007672 Unchecked 6
- 10.6019/CHEMBL5303304 U2OS 5
23126648 10.1021/jm301048a Unchecked 4
- 10.6019/CHEMBL5303304 Fibroblast 4
21919481 10.1021/jm2007672 Neuronal acetylcholine receptor subunit alpha-7 4
- 10.6019/CHEMBL5303304 HEK-293T 4
23126648 10.1021/jm301048a 5-hydroxytryptamine receptor 3A 4
23126648 10.1021/jm301048a Neuronal acetylcholine receptor subunit alpha-7 4
21919481 10.1021/jm2007672 5-hydroxytryptamine receptor 3A 3
23126648 10.1021/jm301048a Rattus norvegicus 3
23126648 10.1021/jm301048a Mus musculus 2
23126648 10.1021/jm301048a Neuronal acetylcholine receptor; alpha4/beta2 2
23126648 10.1021/jm301048a ADMET 2
23126648 10.1021/jm301048a Cytochrome P450 3A4 2
20828128 10.1021/jm100834y Acetylcholine-binding protein 2
21919481 10.1021/jm2007672 Rattus norvegicus 2
23126648 10.1021/jm301048a Cytochrome P450 2B6 1
21919481 10.1021/jm2007672 Mus musculus 1
23126648 10.1021/jm301048a Cytochrome P450 2C19 1
- 10.6019/CHEMBL5665443 Uracil-DNA glycosylase 1

Data from ChEMBL 36 via Core Engine