Compound: berberine
SMILES: O1c2c(cc3CC[n+]4c(-c3c2)cc5ccc(c(c5c4)OC)OC)OC1
InChIKey: YBHILYKTIRIUTE-UHFFFAOYSA-N
Synonyms: berberine, 2086-83-1, Umbellatine, Berberin, Berbericine, Majarine, Thalsine, Umbellatin, Berberone, 0I8Y3P32UF, DTXSID9043857, Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, 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, CHEBI:16118, 9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium, 5,6-DIHYDRO-9,10-DIMETHOXY-1,3-BENZODIOXOLO(5,6-A)BENZO(G)QUINOLIZINIUM, 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$l^(5)-azapentacyclo(11.8.0.0^(2,10).0^(4,8).0^(15,20))henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium, 16,17-dimethoxy-5,7-dioxa-13$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, 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, RefChem:5599, DTXCID7023857, 218-229-1, 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium, MFCD01175817, 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, Berberal, ST055798, 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetrahydroberbinium, CHEMBL12089, 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[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, C20H18NO4, 5,6-DIHYDRO-9,10-DIMETHOXYBENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM, EINECS 218-229-1, Umbellatine (6CI), BRN 3570374, Spectrum_001110, 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], 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium, BERBERINE [MART.], UPCMLD-DP032, NCIMech_000354, BERBERINE [WHO-DD], UNII-0I8Y3P32UF, SCHEMBL25632, BSPBio_000432, BSPBio_002156, KBioGR_001230, KBioSS_001590, cid_12456, DivK1c_000265, inverted exclamation markY97%, SPBio_000708, SPBio_002651, BPBio1_000476, CHEMBL295124, MEGxp0_001923, orb1302341, SCHEMBL29354144, SCHEMBL30153843, UPCMLD-DP032:001, ACon1_001957, BCBcMAP01_000112, GTPL11353, KBio1_000265, KBio2_001590, KBio2_004158, KBio2_006726, KBio3_001656, NINDS_000265, 34MD1011DM, HMS3561D13, HMS5086K15, HY-N0716, AC-117, BBL029198, BDBM50203126, CCG-35898, s9046, STK870320, 5,6-dihydro-9,10-dimethoxy-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, AKOS002141363, DB04115, SDCCGMLS-0066718.P001, BERBINIUM, 7,8,13,13a-TETRAHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-, IDI1_000265, SMP1_000298, NCGC00016526-01, NCGC00016526-03, NCGC00016526-04, NCGC00016526-05, NCGC00016526-06, NCGC00016526-08, NCGC00016526-11, NCGC00016526-13, NCGC00016526-19, NCGC00091896-03, NCI60_001050, NCI60_001224, NCI60_004319, SY232626, SBI-0051613.P002, DB-050153, CS-0009734, NS00009669, C00757, 2,3-methylenedioxy-9,10-dimethoxy-protoberberine, Q176525, BERBERINE (CONSTITUENT OF GOLDENSEAL) [DSC], SR-01000711827-5, BRD-K14796088-003-06-0, BRD-K14796088-003-17-7, BRD-K14796088-003-25-0, BRD-K14796088-003-26-8, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium, 9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium, 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-2H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium, 9,10-dimethoxy-5,6-dihydro-2H-1,3-dioxoleno[4,5-g]isoquinolino[3,2-a]isoquinol ine, 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), 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+
Theoretical properties:
molecular_formula: C20H18NO4+
molecular_weight: 336.4 g/mol
exact_mass: 336.12358306 g/mol
formal_charge: 1
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 25
topological_polar_surface_area: 40.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Berberine is a berberine alkaloid, an organic heteropentacyclic compound, an alkaloid antibiotic and a botanical anti-fungal agent. It has a role as a geroprotector, an antioxidant, a metabolite, a hypoglycemic agent, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an antineoplastic agent, an antilipemic drug, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, a potassium channel blocker, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor and an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor.", "chebi": null, "chembl": "BERBERINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Berberine is an organic compound classified as benzylisoquinoline alkaloid. Chemically, it is a quaternary ammonia compound.\nIts name is derived from the genus of plants, Berberis. Berberine occurs in the roots, bark, stems, and leaves of Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal).\nDue to their yellow pigmentation, raw Berberis materials were once commonly used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence. As a natural dye, berberine has a color index of 75160.\nPlants containing berberine have been used in traditional medicine, and berberine extracts are sold as dietary supplements. Other than in China as an over-the-counter drug, berberine is not approved as a prescription drug, regulated or proven safe in any country."}