9-O-[3-(4-Chloro-phenoxyl)propyl]-berberine bromide

ID: ALA1164137

Chembl Id: CHEMBL1164137

PubChem CID: 46907294

Max Phase: Preclinical

Molecular Formula: C28H25BrClNO5

Molecular Weight: 490.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2cc3[n+](cc2c1OCCCOc1ccc(Cl)cc1)CCc1cc2c(cc1-3)OCO2.[Br-]

Standard InChI:  InChI=1S/C28H25ClNO5.BrH/c1-31-25-8-3-18-13-24-22-15-27-26(34-17-35-27)14-19(22)9-10-30(24)16-23(18)28(25)33-12-2-11-32-21-6-4-20(29)5-7-21;/h3-8,13-16H,2,9-12,17H2,1H3;1H/q+1;/p-1

Standard InChI Key:  ZPAUPGVRHFKPAD-UHFFFAOYSA-M

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 490.96

Molecular Weight (Monoisotopic): 490.1416

AlogP: 5.59

#Rotatable Bonds: 7

Polar Surface Area: 50.03

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.02

CX LogD: 1.02

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.25

Np Likeness Score: 0.57

References

1. Huang L, Luo Z, He F, Lu J, Li X..  (2010)  Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase.,  18  (12): [PMID:20471843] [10.1016/j.bmc.2010.04.063]

2. Haranahalli K, Tong S, Ojima I..  (2016)  Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.,  24  (24): [PMID:27189886] [10.1016/j.bmc.2016.05.003]

3. Buroni S, Makarov V, Scoffone VC, Trespidi G, Riccardi G, Chiarelli LR..  (2020)  The cell division protein FtsZ as a cellular target to hit cystic fibrosis pathogens.,  190  [PMID:32066012] [10.1016/j.ejmech.2020.112132]

Source

Source(1):

• Scientific Literature