ID: ALA464249

Max Phase: Preclinical

Molecular Formula: C14H11ClN2O5

Molecular Weight: 322.70

Molecule Type: Small molecule

Representations

Synonyms (2): TCMDC-124051 | TCMDC-124051
Synonyms from Alternative Forms(2):

Canonical SMILES:  COc1cc([N+](=O)[O-])ccc1NC(=O)c1cc(Cl)ccc1O

Standard InChI:  InChI=1S/C14H11ClN2O5/c1-22-13-7-9(17(20)21)3-4-11(13)16-14(19)10-6-8(15)2-5-12(10)18/h2-7,18H,1H3,(H,16,19)

Standard InChI Key:  SIWASSLWJNRVAY-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: 322.70

Molecular Weight (Monoisotopic): 322.0356

AlogP: 3.21

#Rotatable Bonds: 4

Polar Surface Area: 101.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.89

CX Basic pKa:

CX LogP: 3.15

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: -1.69

References

1. Coi A, Fiamingo FL, Livi O, Calderone V, Martelli A, Massarelli I, Bianucci AM..  (2009)  QSAR studies on BK channel activators.,  17  (1): [PMID:19026552] [10.1016/j.bmc.2008.10.068]

2. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

3. 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]

4. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

5. 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]

Source

Source(3):

• Scientific Literature
• GSK Malaria Screening
• St Jude Leishmania Screening