ID: ALA476327

Max Phase: Preclinical

Molecular Formula: C19H16ClNO3

Molecular Weight: 306.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc2cc3[n+](cc2c1)CCc1cc2c(cc1-3)OCO2.[Cl-]

Standard InChI:  InChI=1S/C19H16NO3.ClH/c1-21-15-3-2-12-7-17-16-9-19-18(22-11-23-19)8-13(16)4-5-20(17)10-14(12)6-15;/h2-3,6-10H,4-5,11H2,1H3;1H/q+1;/p-1

Standard InChI Key:  NDIUQNJETGVPRV-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

Properties

Molecular Weight: 306.34

Molecular Weight (Monoisotopic): 306.1125

AlogP: 3.09

#Rotatable Bonds: 1

Polar Surface Area: 31.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: -1.13

CX LogD: -1.13

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: 1.18

References

1. Yang P, Song DQ, Li YH, Kong WJ, Wang YX, Gao LM, Liu SY, Cao RQ, Jiang JD..  (2008)  Synthesis and structure-activity relationships of berberine analogues as a novel class of low-density-lipoprotein receptor up-regulators.,  18  (16): [PMID:18644725] [10.1016/j.bmcl.2008.07.005]

2. Xu B, Jiang X, Xiong J, Lan J, Tian Y, Zhong L, Wang X, Xu N, Cao H, Zhang W, Zhang H, Hong X, Zhan YY, Zhang Y, Hu T..  (2020)  Structure-Activity Relationship Study Enables the Discovery of a Novel Berberine Analogue as the RXRα Activator to Inhibit Colon Cancer.,  63  (11): [PMID:32391701] [10.1021/acs.jmedchem.0c00088]

Source

Source(1):

• Scientific Literature