BRADANICLINE

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Search structure


Synonyms	ATA-101 Bradanicline TC 5619 TC-5619
Status
Molecule Category	UNKNOWN
UNII	UM3821998K
EPA CompTox	DTXSID40213778


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	OXKRFEWMSWPKKV-GHTZIAJQSA-N
Smiles	O=C(N[C@@H]1C2CCN(CC2)[C@H]1Cc1cccnc1)c1cc2ccccc2o1
InChI	InChI=1S/C22H23N3O2/c26-22(20-13-17-5-1-2-6-19(17)27-20)24-21-16-7-10-25(11-8-16)18(21)12-15-4-3-9-23-14-15/h1-6,9,13-14,16,18,21H,7-8,10-12H2,(H,24,26)/t18-,21+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H23N3O2
Molecular Weight	361.45
AlogP	3.26
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	4.0
Polar Surface Area	58.37
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	27.0

Bioactivity

Mechanism of Action	Action	Reference
Neuronal acetylcholine receptor protein alpha-7 subunit agonist	AGONIST	PubMed PubMed


Protein: Neuronal acetylcholine receptor protein alpha-7 subunit Description: Neuronal acetylcholine receptor subunit alpha-7 Organism : Homo sapiens P36544 ENSG00000175344

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Ligand-gated ion channel 5HT3 receptor	-	-	-	-	25-25
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor alpha subunit	17	-	-	1-3	-
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor beta subunit	-	-	-	1700	-
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	54000	-	-	-
Unclassified protein	-	-	20	15	-

Assay Description	Organism	Bioactivity	Reference
Binding affinity to Lymnaea stagnalis His6-AChBP expressed in Bac-to-Bac baculovirus expression system by surface plasmon resonance biosensor assay	Lymnaea stagnalis	19.95 nM
Displacement of [3H]epibatidine from Lymnaea stagnalis His6-AChBP expressed in Bac-to-Bac baculovirus expression system	Lymnaea stagnalis	14.45 nM
Displacement of [3H]-MLA from human alpha7 nAChR expressed in human SH-SY5Y cells	Homo sapiens	2.754 nM
Binding affinity to human 5HT3 receptor at 10 uM by radioligand binding assay	Homo sapiens	25.0 %
Binding affinity to mouse 5HT3 receptor at 10 uM by radioligand binding assay	Mus musculus	59.0 %
Inhibition of sodium channel site 2	None	79.0 %
Inhibition of non-selective opioid receptor	None	58.0 %
Binding affinity to alpha7 nAChR in rat hippocampal membranes	Rattus norvegicus	1.0 nM
Agonist activity at human alpha7 nAChR expressed in Xenopus oocyte	Homo sapiens	33.0 nM
Binding affinity to human alpha7 nAChR expressed in HEK293 cells co-expressing RIC3 cDNA	Homo sapiens	1.0 nM
Inhibition of Sodium channel site 2	None	50.0 %
Inhibition of mouse 5HT3R at 10 uM by radioligand displacement assay	Mus musculus	59.0 %
Inhibition of human 5HT3R at 10 uM	Homo sapiens	25.0 %
Displacement of [3H]methyllycaconitine form alpha7 nAchR in rat hippocampal membranes	Rattus norvegicus	0.42 nM
Agonist activity at rat alpha7 nAchR expressed in GH4C1 cells by whole cell patch clamp assay	Rattus norvegicus	17.0 nM
Displacement of [3H]epibatidine form human alpha7 nAchR expressed in HEK293 cells	Homo sapiens	1.0 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL1258006
DrugBank	DB06090
FDA SRS	UM3821998K
Guide to Pharmacology	3969
PubChem	25147644
SureChEMBL	SCHEMBL372929
ZINC	ZINC000064540331

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).