ID: ALA375673

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O

Molecular Weight: 270.72

Molecule Type: Small molecule

Representations

Synonyms (3): TCMDC-125528 | GNF-Pf-1310 | TCMDC-125528
Synonyms from Alternative Forms(3):

Canonical SMILES:  Oc1ccc(Nc2ccnc3cc(Cl)ccc23)cc1

Standard InChI:  InChI=1S/C15H11ClN2O/c16-10-1-6-13-14(7-8-17-15(13)9-10)18-11-2-4-12(19)5-3-11/h1-9,19H,(H,17,18)

Standard InChI Key:  FFAVTICKABAMSV-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: 270.72

Molecular Weight (Monoisotopic): 270.0560

AlogP: 4.34

#Rotatable Bonds: 2

Polar Surface Area: 45.15

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.46

CX Basic pKa: 6.47

CX LogP: 3.87

CX LogD: 3.83

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.68

Np Likeness Score: -0.90

References

1. Dakshanamurthy S, Kim M, Brown ML, Byers SW..  (2007)  In-silico fragment-based identification of novel angiogenesis inhibitors.,  17  (16): [PMID:17591441] [10.1016/j.bmcl.2007.05.104]

2. Acharya BN, Saraswat D, Kaushik MP..  (2008)  Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway.,  43  (12): [PMID:18395298] [10.1016/j.ejmech.2008.02.005]

3. 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]

4. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

5. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

6. PubChem BioAssay data set, 

7. Meister S, Plouffe DM, Kuhen KL, Bonamy GM, Wu T, Barnes SW, Bopp SE, Borboa R, Bright AT, Che J, Cohen S, Dharia NV, Gagaring K, Gettayacamin M, Gordon P, Groessl T, Kato N, Lee MC, McNamara CW, Fidock DA, Nagle A, Nam TG, Richmond W, Roland J, Rottmann M, Zhou B, Froissard P, Glynne RJ, Mazier D, Sattabongkot J, Schultz PG, Tuntland T, Walker JR, Zhou Y, Chatterjee A, Diagana TT, Winzeler EA..  (2011)  Imaging of Plasmodium liver stages to drive next-generation antimalarial drug discovery.,  334  (6061): [PMID:22096101] [10.1126/science.1211936]

8. Acharya BN, Kaushik MP.  (2007)  Pharmacophore-based predictive model generation for potent antimalarials targeting haem detoxification pathway,  16  (5): [10.1007/s00044-007-9025-8]

9. Gozalbes R, Mosulén S, Ortí L, Rodríguez-Díaz J, Carbajo RJ, Melnyk P, Pineda-Lucena A..  (2013)  Hit identification of novel heparanase inhibitors by structure- and ligand-based approaches.,  21  (7): [PMID:23415087] [10.1016/j.bmc.2013.01.033]

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

11. 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. CO-ADD screening of NIH NCI Diversity Set V,  [10.6019/CHEMBL4296182]

12. Willems S, Ohrndorf J, Kilu W, Heering J, Merk D..  (2021)  Fragment-like Chloroquinolineamines Activate the Orphan Nuclear Receptor Nurr1 and Elucidate Activation Mechanisms.,  64  (5.0): [PMID:33629841] [10.1021/acs.jmedchem.0c01779]

Source

Source(6):

• Scientific Literature
• GSK Malaria Screening
• Novartis Malaria Screening
• PubChem BioAssays
• St Jude Leishmania Screening
• CO-ADD antimicrobial screening data