ID: ALA2333219

Max Phase: Preclinical

Molecular Formula: C22H20ClN3O2

Molecular Weight: 393.87

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(CNc2c(CO)cnc3c(C4CC4)cc(C#N)cc23)cc1Cl

Standard InChI:  InChI=1S/C22H20ClN3O2/c1-28-20-5-2-13(8-19(20)23)10-25-21-16(12-27)11-26-22-17(15-3-4-15)6-14(9-24)7-18(21)22/h2,5-8,11,15,27H,3-4,10,12H2,1H3,(H,25,26)

Standard InChI Key:  FGBIHGKWPVSHSO-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: 393.87

Molecular Weight (Monoisotopic): 393.1244

AlogP: 4.75

#Rotatable Bonds: 6

Polar Surface Area: 78.17

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.43

CX LogP: 3.64

CX LogD: 3.35

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -0.81

References

1. Fiorito J, Saeed F, Zhang H, Staniszewski A, Feng Y, Francis YI, Rao S, Thakkar DM, Deng SX, Landry DW, Arancio O..  (2013)  Synthesis of quinoline derivatives: discovery of a potent and selective phosphodiesterase 5 inhibitor for the treatment of Alzheimer's disease.,  60  [PMID:23313637] [10.1016/j.ejmech.2012.12.009]

2. Umar T, Hoda N.  (2015)  Selective inhibitors of phosphodiesterases: therapeutic promise for neurodegenerative disorders,  6  (12): [10.1039/C5MD00419E]

3. Fiorito J, Vendome J, Saeed F, Staniszewski A, Zhang H, Yan S, Deng SX, Arancio O, Landry DW..  (2017)  Identification of a Novel 1,2,3,4-Tetrahydrobenzo[b][1,6]naphthyridine Analogue as a Potent Phosphodiesterase 5 Inhibitor with Improved Aqueous Solubility for the Treatment of Alzheimer's Disease.,  60  (21): [PMID:28985058] [10.1021/acs.jmedchem.7b00979]

4. Das B, Baidya ATK, Mathew AT, Yadav AK, Kumar R..  (2022)  Structural modification aimed for improving solubility of lead compounds in early phase drug discovery.,  56  [PMID:35033884] [10.1016/j.bmc.2022.116614]

Source

Source(1):

• Scientific Literature