16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium

• ChemBase ID: 3737
• Molecular Formular: C20H18NO4+
• Molecular Mass: 336.36122
• Monoisotopic Mass: 336.12358306
• SMILES: COc1ccc2cc3c4cc5c(OCO5)cc4CC[n+]3cc2c1OC
• Canonical SMILES: COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1
• 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/h3-4,7-10H,5-6,11H2,1-2H3/q+1
• InChIKey: YBHILYKTIRIUTE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium; 16,17-dimethoxy-5,7-dioxa-13λ^5-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium
• IUPAC Traditional name: berberine
• Synonyms: BERBERINE, ACETONE ADDUCT; Berberine; umbellatine; 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium; Berberine

Database IDs

• CAS Number: 2086-83-1
• PubChem SID: 160967175; 46506051
• PubChem CID: 2353
• CHEBI ID: 16118
• CHEMBL: 12089
• Chemspider ID: 2263
• DrugBank ID: DB04115
• Unique Ingredient Identifier: 0I8Y3P32UF
• Wikipedia Title: Berberine

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.2833123
• LogD (pH = 7.4): -1.2833123
• Log P: -1.2833123
• Molar Refractivity: 93.5233 cm^3
• Polarizability: 38.453724 Å^3
• Polar Surface Area: 40.8 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.18
• LOG S: -6.02
• Solubility (Water): 3.54e-04 g/l

PROPERTIES

Physical Property

• Solubility: slowly soluble in water
• Apperance: Yellow powder; yellow solid
• Melting Point: 145°C

DETAILS

MP Biomedicals - 05209343

MP Biomedicals Rare Chemical collection

DrugBank - DB04115

• Drug Groups: experimental
• Description: An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [PubChem]