ID: ALA453368

Max Phase: Preclinical

Molecular Formula: C20H18ClNO4

Molecular Weight: 336.37

Molecule Type: Small molecule

Representations

Synonyms (2): Pseudoberberine | Pseudoberberine Chloride
Synonyms from Alternative Forms(2):

Canonical SMILES:  COc1cc2cc3[n+](cc2cc1OC)CCc1cc2c(cc1-3)OCO2.[Cl-]

Standard InChI:  InChI=1S/C20H18NO4.ClH/c1-22-17-7-13-5-16-15-9-20-19(24-11-25-20)6-12(15)3-4-21(16)10-14(13)8-18(17)23-2;/h5-10H,3-4,11H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  BBHLRVYYZRFUGL-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: 336.37

Molecular Weight (Monoisotopic): 336.1230

AlogP: 3.10

#Rotatable Bonds: 2

Polar Surface Area: 40.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: -1.28

CX LogD: -1.28

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: 1.27

References

1. Li YH, Yang P, Kong WJ, Wang YX, Hu CQ, Zuo ZY, Wang YM, Gao H, Gao LM, Feng YC, Du NN, Liu Y, Song DQ, Jiang JD..  (2009)  Berberine analogues as a novel class of the low-density-lipoprotein receptor up-regulators: synthesis, structure-activity relationships, and cholesterol-lowering efficacy.,  52  (2): [PMID:19090767] [10.1021/jm801157z]

2. 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]

3. Wang YX, Wang YP, Zhang H, Kong WJ, Li YH, Liu F, Gao RM, Liu T, Jiang JD, Song DQ..  (2009)  Synthesis and biological evaluation of berberine analogues as novel up-regulators for both low-density-lipoprotein receptor and insulin receptor.,  19  (21): [PMID:19800225] [10.1016/j.bmcl.2009.09.059]

4. Wang YX, Kong WJ, Li YH, Tang S, Li Z, Li YB, Shan YQ, Bi CW, Jiang JD, Song DQ..  (2012)  Synthesis and structure-activity relationship of berberine analogues in LDLR up-regulation and AMPK activation.,  20  (22): [PMID:23058107] [10.1016/j.bmc.2012.09.029]

5. 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