Molecular Details

DICL_CP_0340284 - 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene

Basic Molecular Information

Basic Information

DICL ID

DICL_CP_0340284

PubChem CID

2353

Molecular Formula

C₂₀H₁₈NO₄+

Molecular Weight

336.367 g/mol

Synonyms/Alias

[berberine; 2086-83-1; Umbellatine; Berberin; Berbericine; Majarine; Thalsine; Umbellatin; Berberone; 0I8Y3P32UF; CHEBI:16118; Benzo[g]-1;3-benzodioxolo[5;6-a]quinolizinium; 5;6-dihydro-9;10-dimethoxy...[berberine; 2086-83-1; Umbellatine; Berberin; Berbericine; Majarine; Thalsine; Umbellatin; Berberone; 0I8Y3P32UF; CHEBI:16118; Benzo[g]-1;3-benzodioxolo[5;6-a]quinolizinium; 5;6-dihydro-9;10-dimethoxy-; EINECS 218-229-1; BRN 3570374; UNII-0I8Y3P32UF; Benzo(g)-1;3-benzodioxolo(5;6-a)quinolizinium; 5;6-dihydro-9;10-dimethoxy-; 9;10-Dimethoxy-5;6-dihydro-[1;3]dioxolo[4;5-g]isoquinolino[3;2-a]isoquinolin-7-ium; DTXSID9043857; 9;10-Dimethoxy-2;3-(methylenedioxy)-7;8;13;13a-tetrahydroberbinium; Berberal; 9;10-dimethoxy-5;6-dihydro[1;3]dioxolo[4;5-g]isoquino[3;2-a]isoquinolin-7-ium; 16;17-dimethoxy-5;7-dioxa-13-azoniapentacyclo[11.8.0.02;10.04;8.015;20]henicosa-1(13);2;4(8);9;14;16;18;20-octaene; BERBERINE (MART.); BERBERINE [MART.]; BERBINIUM; 7;8;13;13a-TETRAHYDRO-9;10-DIMETHOXY-2;3-(METHYLENEDIOXY)-; inverted exclamation markY97%; CHEMBL12089; 5;6-Dihydro-9;10-dimethoxybenzo[g]-1;3-benzodioxolo[5;6-a]quinolizinium; 9;10-dimethoxy-2;3-(methylenedioxy)-7;8;13;13a-tetradehydroberbinium; 5;6-DIHYDRO-9;10-DIMETHOXY-1;3-BENZODIOXOLO(5;6-A)BENZO(G)QUINOLIZINIUM; 5;6-DIHYDRO-9;10-DIMETHOXYBENZO(G)-1;3-BENZODIOXOLO(5;6-A)QUINOLIZINIUM; 9;10-DIMETHOXY-5;6-DIHYDRO(1;3)DIOXOLO(4;5-G)ISOQUINO(3;2-A)ISOQUINOLIN-7-IUM; GNF-PF-4545; BER; NSC646666; NCGC00016526-02; NCGC00016526-07; CAS-633-65-8; Berbinium; berberine dimer; Coptis rhizome; Berberinechloride; 7;8;13;13a-tetradehydro-9;10-dimethoxy-2;3-(methylenebis(oxy))berbinium; 7;8;13;13a-tetradehydro-9;10-dimethoxy-2;3-[methylenebis(oxy)]berbinium; C20H18NO4; Umbellatine (6CI); Spectrum_001110; ST055798; Berbinium; 7;8;13;13a-tetradehydro-9;10-dimethoxy-2;3-(methylenedioxy)-; chloride; BERBERINE [MI]; Prestwick0_000586; Prestwick1_000586; Prestwick2_000586; Prestwick3_000586; Spectrum2_000894; Spectrum3_000618; Spectrum4_000785; Spectrum5_001458; BERBERINE [VANDF]; UPCMLD-DP032; NCIMech_000354; BERBERINE [WHO-DD]; SCHEMBL25632; BSPBio_000432; BSPBio_002156; KBioGR_001230; KBioSS_001590; cid_12456; DivK1c_000265; SPBio_000708; SPBio_002651; BPBio1_000476; CHEMBL295124; MEGxp0_001923; Berberin ; Umbellatine; DTXCID7023857; UPCMLD-DP032:001; ACon1_001957; BCBcMAP01_000112; GTPL11353; KBio1_000265; KBio2_001590; KBio2_004158; KBio2_006726; KBio3_001656; NINDS_000265; 34MD1011DM; HMS3561D13; HY-N0716; AC-117; BBL029198; BDBM50203126; CCG-35898; MFCD01175817; s9046; STK870320; 7;8;13;13a-tetradehydro-9;10-dimethoxy-2;3-(methylenedioxy)berbinium; AKOS002141363; DB04115; SDCCGMLS-0066718.P001; 9;10-Dimethoxy-5;6-dihydro-[1;3]dioxolo-[4;5-g]isoquinolino[3;2-a]isoquinolin-7-ium; IDI1_000265; SMP1_000298; NCGC00016526-01; NCGC00016526-03; NCGC00016526-04; NCGC00016526-05; NCGC00016526-06; NCGC00016526-08; NCGC00016526-11; NCGC00016526-13; NCGC00091896-03; NCI60_001050; NCI60_001224; NCI60_004319; SY232626; SBI-0051613.P002; DB-050153; BERBERINE (CONSTITUENT OF GOLDENSEAL); CS-0009734; NS00009669; C00757; A904183; Q176525; BERBERINE (CONSTITUENT OF GOLDENSEAL) [DSC]; Q-200701; Q-200702; SR-01000711827-5; BRD-K14796088-003-06-0; BRD-K14796088-003-17-7; Benzylpenicillin benzathine; Antibiotic for Culture Media Use Only; 5;6-dihydro-9;10-dimethoxy-benzo[g]-1;3-benzodioxolo[5;6-a]quinolizinium; Berbinium; 7;8;13;13a-tetradehydro-9;10-dimethoxy-2;3-(methylenedioxy)-; 3;4-dimethoxy-6;7-dihydro-[1;3]dioxolo[4;5-g]pyrido[2;1-a]isoquinolin-5-ylium; 9;10-Dimethoxy-5;6-dihydro-[1;3]dioxolo[4;5-g]isoquino[3;2-a]isoquinolin-7-ylium; 9;10-Dimethoxy-5;6-dihydro-7lambda~5~-[1;3]dioxolo[4;5-g]isoquino[3;2-a]isoquinoline; Benzo[g]-1;3-benzodioxolo[5;6-a]quinolizinium; 5;6-dihydro-9;10-dimethoxy- (9CI); 16;17-dimethoxy-5;7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2;10}.0^{4;8}.0^{15;20}]henicosa-1(13);2;4(8);9;14;16;18;20-octaen-13-ylium; 9;10-Dimethoxy-5;6-dihydro-[1;3]dioxolo[4;5-g]isoquino[3;2-a]isoquinolin-7-ylium chloride; 9;10-Dimethoxy-5;6-dihydro-[1;3]dioxolo[4;5-g]isoquino[3;2-a]isoquinolin-7-ylium; chloride; InChI=1/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4;7-10H;5-6;11H2;1-2H3/q+]

InChI Key

YBHILYKTIRIUTE-UHFFFAOYSA-N

InChI

InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2...

IUPAC Name

16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene

CAS Number

2086-83-1

Structure Information

Chemical Structure Visualization

SMILES Notation

2D Molecular Drawing

Carbon (C)

Hydrogen (H)

Oxygen (O)

Nitrogen (N)

Sulfur (S)

SDF

25 29 0 0 0 0 0 0 0 0999 V2000
6.9450 -0.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.1731 1.2748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6733 1...

Download SDF File (2283 bytes)

Experimental Data

Activity Data

Target Ion Channel

Inward rectifier potassium channel 4

Uniprot Accession Number

P48050

Function

Inhibitor

Species

Homo sapiens (Human)

IC₅₀

IC₅₀: 5330 nM

EC₅₀

N/A (Not available)

K_i

N/A (Not available)

K_d

N/A (Not available)

Inhibition

N/A (Not available)

Experimental Conditions

pH 7.4

Holding Potential

−80 mV mV

Temperature

20−25 °C

Test Method

Patch-clamping

Test Species

RPMI-8226

Binding Information

Binding Site

Not specified

Binding Site Residue

Not specified

Disease Information

Related Disease

Not specified

References

DOI

10.1016/s0024-3205(98)00209-4

URL

N/A (Not available)

PMID

9651117

Patent

N/A (Not available)

Computed Properties

Heavy Atom Count

Rotatable Bonds

logP

3.0963

Complexity

92.51

TPSA (Å²)

40.8

H-Bond Donors

H-Bond Acceptors

Ring Count

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