ID: ALA2088010

Max Phase: Preclinical

Molecular Formula: C13H9ClN2O4

Molecular Weight: 292.68

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(Nc1ccc([N+](=O)[O-])cc1)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C13H9ClN2O4/c14-8-1-6-12(17)11(7-8)13(18)15-9-2-4-10(5-3-9)16(19)20/h1-7,17H,(H,15,18)

Standard InChI Key:  HTXGLMUZXAFRII-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: 292.68

Molecular Weight (Monoisotopic): 292.0251

AlogP: 3.21

#Rotatable Bonds: 3

Polar Surface Area: 92.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.89

CX Basic pKa:

CX LogP: 3.31

CX LogD: 2.69

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.67

Np Likeness Score: -1.65

References

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2. Mook RA, Chen M, Lu J, Barak LS, Lyerly HK, Chen W..  (2013)  Small molecule modulators of Wnt/β-catenin signaling.,  23  (7): [PMID:23453073] [10.1016/j.bmcl.2013.01.101]

3. Pauk K, Zadražilová I, Imramovský A, Vinšová J, Pokorná M, Masaříková M, Cížek A, Jampílek J..  (2013)  New derivatives of salicylamides: Preparation and antimicrobial activity against various bacterial species.,  21  (21): [PMID:24045008] [10.1016/j.bmc.2013.08.029]

4. Mook RA, Wang J, Ren XR, Chen M, Spasojevic I, Barak LS, Lyerly HK, Chen W..  (2015)  Structure-activity studies of Wnt/β-catenin inhibition in the Niclosamide chemotype: Identification of derivatives with improved drug exposure.,  23  (17): [PMID:26272032] [10.1016/j.bmc.2015.07.001]

5. Pospisilova S, Michnova H, Kauerova T, Pauk K, Kollar P, Vinsova J, Imramovsky A, Cizek A, Jampilek J..  (2018)  In vitro activity of salicylamide derivatives against vancomycin-resistant enterococci.,  28  (12): [PMID:29773506] [10.1016/j.bmcl.2018.05.011]

6. Xu J, Berastegui-Cabrera J, Chen H, Pachón J, Zhou J, Sánchez-Céspedes J..  (2020)  Structure-Activity Relationship Studies on Diversified Salicylamide Derivatives as Potent Inhibitors of Human Adenovirus Infection.,  63  (6): [PMID:32045239] [10.1021/acs.jmedchem.9b01950]

7. Tian M, Abdelrahman A, Baqi Y, Fuentes E, Azazna D, Spanier C, Densborn S, Hinz S, Schmid R, Müller CE..  (2020)  Discovery and Structure Relationships of Salicylanilide Derivatives as Potent, Non-acidic P2X1 Receptor Antagonists.,  63  (11): [PMID:32345019] [10.1021/acs.jmedchem.0c00435]

8. Shamim K, Xu M, Hu X, Lee EM, Lu X, Huang R, Shah P, Xu X, Chen CZ, Shen M, Guo H, Chen L, Itkin Z, Eastman RT, Shinn P, Klumpp-Thomas C, Michael S, Simeonov A, Lo DC, Ming GL, Song H, Tang H, Zheng W, Huang W..  (2021)  Application of niclosamide and analogs as small molecule inhibitors of Zika virus and SARS-CoV-2 infection.,  40  [PMID:33689873] [10.1016/j.bmcl.2021.127906]

9. Juang YP, Chou YT, Lin RX, Ma HH, Chao TL, Jan JT, Chang SY, Liang PH..  (2022)  Design, synthesis and biological evaluations of niclosamide analogues against SARS-CoV-2.,  235  [PMID:35344901] [10.1016/j.ejmech.2022.114295]

Source

Source(1):

• Scientific Literature