ID: ALA541672

Max Phase: Preclinical

Molecular Formula: C27H25ClN2O3

Molecular Weight: 425.51

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc2cc3[n+](cc2c1NCCc1ccccc1)CCc1cc2c(cc1-3)OCO2.[Cl-]

Standard InChI:  InChI=1S/C27H24N2O3.ClH/c1-30-24-8-7-19-13-23-21-15-26-25(31-17-32-26)14-20(21)10-12-29(23)16-22(19)27(24)28-11-9-18-5-3-2-4-6-18;/h2-8,13-16H,9-12,17H2,1H3;1H

Standard InChI Key:  OXNNJOPPFIDIDT-UHFFFAOYSA-N

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

Properties

Molecular Weight: 425.51

Molecular Weight (Monoisotopic): 425.1860

AlogP: 4.74

#Rotatable Bonds: 5

Polar Surface Area: 43.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 2.86

CX LogP: 0.36

CX LogD: 0.36

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: 0.66

References

1. Ma Y, Ou TM, Hou JQ, Lu YJ, Tan JH, Gu LQ, Huang ZS..  (2008)  9-N-Substituted berberine derivatives: stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc.,  16  (16): [PMID:18674916] [10.1016/j.bmc.2008.07.029]

2. Shan WJ, Huang L, Zhou Q, Meng FC, Li XS..  (2011)  Synthesis, biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant, inhibitors of acetylcholinesterase, butyrylcholinesterase and amyloid-β aggregation.,  46  (12): [PMID:22019228] [10.1016/j.ejmech.2011.09.051]

3. Wang SK, Wu Y, Wang XQ, Kuang GT, Zhang Q, Lin SL, Liu HY, Tan JH, Huang ZS, Ou TM..  (2017)  Discovery of Small Molecules for Repressing Cap-Independent Translation of Human Vascular Endothelial Growth Factor (hVEGF) as Novel Antitumor Agents.,  60  (13): [PMID:28530833] [10.1021/acs.jmedchem.6b01444]

Source

Source(1):

• Scientific Literature