1-(3-(aminomethyl)phenyl)-N-(2-fluoro-4-(piperidin-1-yl)phenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

ID: ALA4873298

PubChem CID: 164620396

Max Phase: Preclinical

Molecular Formula: C23H23F4N5O

Molecular Weight: 461.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCc1cccc(-n2nc(C(F)(F)F)cc2C(=O)Nc2ccc(N3CCCCC3)cc2F)c1

Standard InChI:  InChI=1S/C23H23F4N5O/c24-18-12-16(31-9-2-1-3-10-31)7-8-19(18)29-22(33)20-13-21(23(25,26)27)30-32(20)17-6-4-5-15(11-17)14-28/h4-8,11-13H,1-3,9-10,14,28H2,(H,29,33)

Standard InChI Key:  SQZUMCHVWJKWOG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.2635  -13.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2624  -14.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9704  -14.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6801  -14.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6772  -13.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9686  -13.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3884  -14.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0955  -14.4903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9662  -12.4474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6200  -11.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3652  -11.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5479  -11.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2978  -11.9681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0655  -10.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3956   -9.7830    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.2531  -10.6184    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4807   -9.9466    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.3986  -12.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5729  -13.0108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0028  -11.6622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7814  -11.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9525  -12.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7303  -12.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3354  -12.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1576  -11.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3801  -11.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1114  -12.6505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2017  -10.5610    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.2824  -13.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0544  -13.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6580  -13.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4844  -12.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7071  -12.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 26 28  1  0
 27 29  1  0
 27 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873298

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 461.46

Molecular Weight (Monoisotopic): 461.1839

AlogP: 4.73

#Rotatable Bonds: 5

Polar Surface Area: 76.18

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.67

CX Basic pKa: 9.25

CX LogP: 4.56

CX LogD: 2.73

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.54

Np Likeness Score: -1.85

References

1. Kotian PL, Wu M, Vadlakonda S, Chintareddy V, Lu P, Juarez L, Kellogg-Yelder D, Chen X, Muppa S, Chambers-Wilson R, Davis Parker C, Williams J, Polach KJ, Zhang W, Raman K, Babu YS..  (2021)  Berotralstat (BCX7353): Structure-Guided Design of a Potent, Selective, and Oral Plasma Kallikrein Inhibitor to Prevent Attacks of Hereditary Angioedema (HAE).,  64  (17.0): [PMID:34436898] [10.1021/acs.jmedchem.1c00511]

Source

Source(1):

• Scientific Literature