ID: ALA108922

Max Phase: Preclinical

Molecular Formula: C21H28N4O2

Molecular Weight: 368.48

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCO/N=C/c1ccc(OCCC2CCN(c3ccc(C)nn3)CC2)cc1

Standard InChI:  InChI=1S/C21H28N4O2/c1-3-27-22-16-19-5-7-20(8-6-19)26-15-12-18-10-13-25(14-11-18)21-9-4-17(2)23-24-21/h4-9,16,18H,3,10-15H2,1-2H3/b22-16+

Standard InChI Key:  LNKHWGSSSPTTHB-CJLVFECKSA-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: 368.48

Molecular Weight (Monoisotopic): 368.2212

AlogP: 3.84

#Rotatable Bonds: 8

Polar Surface Area: 59.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 4.47

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -1.62

References

1. Watson KG, Brown RN, Cameron R, Chalmers DK, Hamilton S, Jin B, Krippner GY, Luttick A, McConnell DB, Reece PA, Ryan J, Stanislawski PC, Tucker SP, Wu WY, Barnard DL, Sidwell RW..  (2003)  An orally bioavailable oxime ether capsid binder with potent activity against human rhinovirus.,  46  (15): [PMID:12852746] [10.1021/jm0202876]

2. Brown RN, Cameron R, Chalmers DK, Hamilton S, Luttick A, Krippner GY, McConnell DB, Nearn R, Stanislawski PC, Tucker SP, Watson KG..  (2005)  2-Ethoxybenzoxazole as a bioisosteric replacement of an ethyl benzoate group in a human rhinovirus (HRV) capsid binder.,  15  (8): [PMID:15808466] [10.1016/j.bmcl.2005.02.054]

3. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

4. Wang H, Xiao J, Gao D, Zhang X, Yan H, Gong Z, Sun T, Li S..  (2011)  Pharmacophore-based design, synthesis, and biological evaluation of novel chloro-pyridazine piperazines as human rhinovirus (HRV-3) inhibitors.,  21  (3): [PMID:21215622] [10.1016/j.bmcl.2010.12.001]

5. Feil SC, Hamilton S, Krippner GY, Lin B, Luttick A, McConnell DB, Nearn R, Parker MW, Ryan J, Stanislawski PC, Tucker SP, Watson KG, Morton CJ..  (2012)  An Orally Available 3-Ethoxybenzisoxazole Capsid Binder with Clinical Activity against Human Rhinovirus.,  3  (4): [PMID:24900468] [10.1021/ml2002955]

6. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

7. Egorova A, Ekins S, Schmidtke M, Makarov V..  (2019)  Back to the future: Advances in development of broad-spectrum capsid-binding inhibitors of enteroviruses.,  178  [PMID:31226653] [10.1016/j.ejmech.2019.06.008]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data