ID: ALA549220

Max Phase: Preclinical

Molecular Formula: C15H15FN2O3

Molecular Weight: 290.29

Molecule Type: Small molecule

Representations

Synonyms (3): TCMDC-123812 | OSM-S-05 | TCMDC-123812
Synonyms from Alternative Forms(3):

Canonical SMILES:  Cc1cc(C(=O)OCC(N)=O)c(C)n1-c1ccc(F)cc1

Standard InChI:  InChI=1S/C15H15FN2O3/c1-9-7-13(15(20)21-8-14(17)19)10(2)18(9)12-5-3-11(16)4-6-12/h3-7H,8H2,1-2H3,(H2,17,19)

Standard InChI Key:  YSUCFIZUNLQZDX-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: 290.29

Molecular Weight (Monoisotopic): 290.1067

AlogP: 1.88

#Rotatable Bonds: 4

Polar Surface Area: 74.32

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.15

CX LogD: 2.15

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: -2.06

References

1. 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]

2. Vicky Avery (a), Jonathan Baell (b), Sanjay Batra (c), Jeremy Burrows (d), Soumya Bhattacharyya (c), Felix Calderon (e), Sue Charman(b), James R. Cronshaw (g), Sergio Wittlin (f), Matin Dean (g), Sandra Duffy (a), Sabine Fletcher (a), Javier Gamo (e), Zoe Hungerford (g), James Pham (h), Stuart Ralph (h), Murray N. Robertson (g), Matthew Tarnowski (g), Matthew H. Todd (g), Alice E. Williamson (g), Paul Willis (d), Karen White (b), Laura White (g), Paul M.Ylioja (g). (a) Discovery Biology, Eskitis Institute for Cell and Molecular Therapies, Griffith University, Nathan, QLD 4111, Australia; (b) Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, VIC 3052, Australia; (c) Medicinal Chemistry Division, Central Drug Research Institute, PO Box 173, Lucknow, 226 001, India; (d) Medicines for Malaria Venture, PO Box 1826, 20 rte de Pré-Bois, 1215 Geneva 15, Switzerland; (e) Tres Cantos Medicines Development Campus, Diseases of the Developing World (DDW), GlaxoSmithKline, Severo Ochoa 2, 28760 Tres Cantos, Spain; (f) Swiss Tropical and Public Health Institute, Socinstr. 57, 4051 Basel, Switzerland; (g) School of Chemistry, The University of Sydney, NSW 2006, Australia; (h) Department of Biochemistry & Molecular Biology, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, 3010, Australia.. Open Source Malaria Deposition 1. http://malaria.ourexperiment.org,  [10.6019/CHEMBL2113921]

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

4. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper, Alice Williamson, Matthew Todd. CO-ADD antimicrobial screening data of OSM samples,  [10.6019/CHEMBL3832881]

Source

Source(4):

• GSK Malaria Screening
• Open Source Malaria Screening
• St Jude Leishmania Screening
• CO-ADD antimicrobial screening data