16-hydroxy-17-methoxy-5,7-dioxa-13λ5-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-13-ylium bromide

• ChemBase ID: 165615
• Molecular Formular: C19H14BrNO4
• Molecular Mass: 400.22276
• Monoisotopic Mass: 399.01061993
• SMILES: c1c(c(c2c(c1)cc1[n+](c2)ccc2c1cc1c(c2)OCO1)O)OC.[Br-]
• Canonical SMILES: COc1ccc2c(c1O)c[n+]1c(c2)c2cc3OCOc3cc2cc1.[Br-]
• InChI: InChI=1S/C19H13NO4.BrH/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21;/h2-9H,10H2,1H3;1H
• InChIKey: CZRIPWYMXMLIFR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 16-hydroxy-17-methoxy-5,7-dioxa-13λ^5-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-13-ylium bromide
• IUPAC Traditional name: 16-hydroxy-17-methoxy-5,7-dioxa-13λ^5-azapentacyclo[11.8.0.0^2,^1^0.0^4,^8.0^1^5,^2^0]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-13-ylium bromide
• Synonyms: 9-Hydroxy-10-methoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium Bromide; Dehydro Berberrubine Bromide

Database IDs

• CAS Number: 57721-67-2
• PubChem SID: 162259748
• PubChem CID: 71315299

CALCULATED PROPERTIES

• Acid pKa: 8.09081
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.4978791
• LogD (pH = 7.4): 1.8236544
• Log P: 0.33697262
• Molar Refractivity: 89.5951 cm^3
• Polarizability: 37.12051 Å^3
• Polar Surface Area: 52.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229315

An analogue of Berberrubine, which is one of the main metabolite of Berberine. It showed neoplasm inhibiting and antileukemic activities in mice.

REFERENCES

• Kim, S.H., et al.: Life Sci., 70, 1299 (2002)
• Hao, H., et al.: Curr. Drug Metab., 8, 137 (2002)