N-[1-(4-Cyano-3-fluoro-benzyl)-1H-pyrazol-3-yl]-2-(4-dimethylamino-phenyl)-acetamide

ID: ALA4218161

PubChem CID: 118560191

Max Phase: Preclinical

Molecular Formula: C21H20FN5O

Molecular Weight: 377.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(CC(=O)Nc2ccn(Cc3ccc(C#N)c(F)c3)n2)cc1

Standard InChI:  InChI=1S/C21H20FN5O/c1-26(2)18-7-4-15(5-8-18)12-21(28)24-20-9-10-27(25-20)14-16-3-6-17(13-23)19(22)11-16/h3-11H,12,14H2,1-2H3,(H,24,25,28)

Standard InChI Key:  CIDJQFWRYYESJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   40.8802  -26.1253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5473  -25.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2929  -24.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4716  -24.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2131  -25.6433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2546  -26.0552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.9672  -25.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6782  -26.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9688  -24.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.3867  -25.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4976  -26.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7930  -25.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8030  -24.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0950  -24.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3792  -24.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3756  -25.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0842  -26.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0961  -26.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8082  -25.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8102  -24.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0942  -24.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3850  -24.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5177  -24.4238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   47.2257  -24.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5171  -23.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6660  -26.0339    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.6775  -24.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9728  -23.9793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  3  1  0
  1  2  2  0
  3  4  2  0
  5  1  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 10  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 16 26  1  0
 27 28  3  0
 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4218161

   N-[1-[(4-cyano-3-fluorophenyl)methyl]pyrazol-3-yl]-2-[4-(dimethylamino)phenyl]acetamide

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

Calculated Properties

Molecular Weight: 377.42

Molecular Weight (Monoisotopic): 377.1652

AlogP: 3.19

#Rotatable Bonds: 6

Polar Surface Area: 73.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.30

CX Basic pKa: 4.89

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.72

Np Likeness Score: -2.56

References

1. Bezençon O, Heidmann B, Siegrist R, Stamm S, Richard S, Pozzi D, Corminboeuf O, Roch C, Kessler M, Ertel EA, Reymond I, Pfeifer T, de Kanter R, Toeroek-Schafroth M, Moccia LG, Mawet J, Moon R, Rey M, Capeleto B, Fournier E..  (2017)  Discovery of a Potent, Selective T-type Calcium Channel Blocker as a Drug Candidate for the Treatment of Generalized Epilepsies.,  60  (23): [PMID:29116786] [10.1021/acs.jmedchem.7b01236]

Source

Source(1):

• Scientific Literature