ID: ALA542642

Max Phase: Preclinical

Molecular Formula: C21H25ClN2O3

Molecular Weight: 352.43

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cl.O=C(O)[C@@H]1CCCN(CCON=C(c2ccccc2)c2ccccc2)C1

Standard InChI:  InChI=1S/C21H24N2O3.ClH/c24-21(25)19-12-7-13-23(16-19)14-15-26-22-20(17-8-3-1-4-9-17)18-10-5-2-6-11-18;/h1-6,8-11,19H,7,12-16H2,(H,24,25);1H/t19-;/m1./s1

Standard InChI Key:  RPWCLFUNNRFLDQ-FSRHSHDFSA-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: 352.43

Molecular Weight (Monoisotopic): 352.1787

AlogP: 3.25

#Rotatable Bonds: 7

Polar Surface Area: 62.13

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.33

CX Basic pKa: 8.15

CX LogP: 1.34

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -0.60

References

1. Andersen KE, Sørensen JL, Lau J, Lundt BF, Petersen H, Huusfeldt PO, Suzdak PD, Swedberg MD..  (2001)  Synthesis of novel gamma-aminobutyric acid (GABA) uptake inhibitors. 5.(1) Preparation and structure-activity studies of tricyclic analogues of known GABA uptake inhibitors.,  44  (13): [PMID:11405652] [10.1021/jm990513k]

2. Knutsen LJ, Andersen KE, Lau J, Lundt BF, Henry RF, Morton HE, Naerum L, Petersen H, Stephensen H, Suzdak PD, Swedberg MD, Thomsen C, Sørensen PO..  (1999)  Synthesis of novel GABA uptake inhibitors. 3. Diaryloxime and diarylvinyl ether derivatives of nipecotic acid and guvacine as anticonvulsant agents.,  42  (18): [PMID:10479278] [10.1021/jm981027k]

3. Andersen KE, Sørensen JL, Huusfeldt PO, Knutsen LJ, Lau J, Lundt BF, Petersen H, Suzdak PD, Swedberg MD..  (1999)  Synthesis of novel GABA uptake inhibitors. 4. Bioisosteric transformation and successive optimization of known GABA uptake inhibitors leading to a series of potent anticonvulsant drug candidates.,  42  (21): [PMID:10543872] [10.1021/jm980492e]

Source

Source(1):

• Scientific Literature