Molecular Details

DICL_CP_0335904 - (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

Basic Molecular Information

Basic Information

DICL ID

DICL_CP_0335904

PubChem CID

441074

Molecular Formula

C₂₀H₂₄N₂O₂

Molecular Weight

324.424 g/mol

Synonyms/Alias

[quinidine; 56-54-2; (+)-Quinidine; Conquinine; Pitayine; Chinidin; Conchinin; (8R;9S)-Quinidine; (9S)-6-Methoxycinchonan-9-ol; beta-Quinine; Quinidex; Kinidin; Conchinine; Cin-Quin; beta-Quinidine; c...[quinidine; 56-54-2; (+)-Quinidine; Conquinine; Pitayine; Chinidin; Conchinin; (8R;9S)-Quinidine; (9S)-6-Methoxycinchonan-9-ol; beta-Quinine; Quinidex; Kinidin; Conchinine; Cin-Quin; beta-Quinidine; chinidinum; quinidina; Quinicardine; Quinora; (S)-[(2R;4S;5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol; Cinchonan-9-ol; 6-methoxy-; (9S)-; Chinidine; CHEBI:28593; alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol; .beta.-Quinidine; UNII-ITX08688JL; Quinaglute; CCRIS 672; Quiniduran; Auriquin; HSDB 225; ITX08688JL; DTXSID4023549; Quinidine sulfate; NCI-C56246; EINECS 200-279-0; 6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol; CHEMBL1294; Quinact; (1S)-(6-Methoxyquinolin-4-yl)((2R;4S;5R)-5-vinylquinuclidin-2-yl)methanol; DTXCID70819883; MFCD00135581; Quinidine (>85%); alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol (9S)-; (9S)-6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol; (S)-(6-methoxyquinolin-4-yl)((2R;5R)-5-vinylquinuclidin-2-yl)methanol; (3.alpha.; 9S)-6-Methoxycinchonan-9-ol; QUINIDINE (MART.); QUINIDINE [MART.]; (R)-(6-methoxyquinolin-4-yl)((3S;4R;7S)-3-vinylquinuclidin-7-yl)methanol; TCMDC-131239; (S)-(6-methoxy-4-quinolyl)-[(2R;4S;5R)-5-vinylquinuclidin-2-yl]methanol; (S)-(6-Methoxy-quinolin-4-yl)-((2R;5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; (S)-(6-methoxyquinolin-4-yl)((1S;2R;4S;5R)-5-vinylquinuclidin-2-yl)methanol; (S)-[(4S;5R;7R)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol; CAS-56-54-2; Chinidin [German]; (S)-((2S;4S;5R)-5-ETHENYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(6-METHOXYQUINOLIN-4-YL)METHANOL; SMR000857275; Quinidine [BAN:NF]; Quinidine (may contain up to 15% of dihydroquinidine); Quinindine; (8R;9S)-6-Methoxycinchonan-9-ol; (S)-(6-Methoxy-quinolin-4-yl)-((2R;5R)-5-vinyl-1-aza-bicyclo(2.2.2)oct-2-yl)-methanol; (S)-[(2R;4S;5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol; Quinidine anhydrous; NCGC00159499-02; QDN; Quinidine; anhydrous; NSC10004; QUINIDINE [MI]; QUINIDINE [HSDB]; Prestwick3_000280; QUINIDINE [VANDF]; bmse000511; Epitope ID:141803; QUINIDINE [WHO-DD]; SCHEMBL15943; BSPBio_000160; MLS001335913; MLS001335914; MLS002548869; BPBio1_000176; GTPL2342; SCHEMBL17537608; LOUPRKONTZGTKE-LHHVKLHASA-N; HMS2234L10; HMS3259O09; NCI-C56426; HY-B1751; Tox21_111720; Tox21_201110; 6-methoxy--(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol; BDBM50121975; AKOS015920101; Tox21_111720_1; CCG-256507; CS-7812; DB00908; NC00478; SDCCGMLS-0066600.P001; NCGC00091231-01; NCGC00091231-02; NCGC00091231-03; NCGC00091231-04; NCGC00091231-18; NCGC00091231-29; NCGC00258662-01; AS-30538; QUININE SULFATE IMPURITY A [WHO-IP]; AB00514657; NS00098768; QUININE BISULFATE IMPURITY A [WHO-IP]; EN300-305202; AB01562940_01; QUININE SULFATE IMPURITY A [EP IMPURITY]; CINCHONAN-9-0L; 6-METHOXY-; (95)-; Q412496; W-109256; BRD-K59632282-052-01-5; BRD-K59632282-052-02-3; BRD-K70799801-311-02-7; QUININE HYDROCHLORIDE IMPURITY A [EP IMPURITY]; Quinidine; crystallized; >=98.0% (dried material; NT); Z1741976976; QUININE BISULFATE HEPTAHYDRATE IMPURITY A [WHO-IP]; 6-METHOXY-ALPHA-(5-VINYL-2-QUINUCLIDINYL)-4-QUINOLINEMETHONOL]

InChI Key

LOUPRKONTZGTKE-LHHVKLHASA-N

InChI

InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6...

IUPAC Name

(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

CAS Number

130-95-0

Structure Information

Chemical Structure Visualization

SMILES Notation

2D Molecular Drawing

Carbon (C)

Hydrogen (H)

Oxygen (O)

Nitrogen (N)

Sulfur (S)

SDF

48 51 0 0 0 0 0 0 0 0999 V2000
5.5463 -2.8098 -0.6714 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2681 -2.2028 -0.8299 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9756 -0.870...

Download SDF File (4100 bytes)

Experimental Data

Activity Data

Target Ion Channel

Connexin 43

Uniprot Accession Number

P17302

Function

Inhibitor

Species

Homo sapiens (Human)

IC₅₀

pIC50: 3.40

EC₅₀

N/A (Not available)

K_i

N/A (Not available)

K_d

N/A (Not available)

Inhibition

N/A (Not available)

Experimental Conditions

Not mention

Holding Potential

−10 mV mV

Temperature

Not mention

Test Method

Patch-clamping

Test Species

HeLa cell

Binding Information

Binding Site

Transmembrane domain

Binding Site Residue

F84, F165, and F169 are highly common residues often found at the exact docking site of these compounds

Disease Information

Related Disease

treatment of cardiac arrhythmias and other dysfunctions

References

DOI

10.3390/biomedicines11071972

URL

N/A (Not available)

PMID

37509611

Patent

N/A (Not available)

Computed Properties

Heavy Atom Count

Rotatable Bonds

logP

3.1732

Complexity

95.0268

TPSA (Å²)

45.59

H-Bond Donors

H-Bond Acceptors

Ring Count

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