(S)-N-(1-(3,4-difluorobenzyl)-1H-pyrazol-3-yl)-2-(6-(3-fluoropyrrolidin-1-yl)pyridin-3-yl)acetamide

ID: ALA4209946

PubChem CID: 118560423

Max Phase: Preclinical

Molecular Formula: C21H20F3N5O

Molecular Weight: 415.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(N2CC[C@H](F)C2)nc1)Nc1ccn(Cc2ccc(F)c(F)c2)n1

Standard InChI:  InChI=1S/C21H20F3N5O/c22-16-5-7-28(13-16)20-4-2-14(11-25-20)10-21(30)26-19-6-8-29(27-19)12-15-1-3-17(23)18(24)9-15/h1-4,6,8-9,11,16H,5,7,10,12-13H2,(H,26,27,30)/t16-/m0/s1

Standard InChI Key:  GYQFUHZEIRPWAL-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   31.7363   -8.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0317   -9.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3162   -8.6149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0577   -7.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2363   -7.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9820   -8.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6491   -9.0969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2747   -9.0268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5621   -8.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8510   -9.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1425   -8.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4332   -9.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7210   -8.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7190   -7.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4350   -7.3947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1443   -7.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5605   -7.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4462   -9.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1503   -8.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1411   -7.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4217   -7.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7205   -7.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8433   -7.3535    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.8626   -8.9920    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.0116   -7.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9232   -6.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1240   -6.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7149   -7.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2614   -7.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9022   -7.2089    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  3  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 17  2  0
  1 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  1  1  0
 20 23  1  0
 19 24  1  0
 14 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
 28 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4209946

   N-[1-[(3,4-difluorophenyl)methyl]pyrazol-3-yl]-2-[6-[(3S)-3-fluoropyrrolidin-1-yl]pyridin-3-yl]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: 415.42

Molecular Weight (Monoisotopic): 415.1620

AlogP: 3.33

#Rotatable Bonds: 6

Polar Surface Area: 63.05

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: 6.14

CX LogP: 3.71

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -2.62

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