1-(3-(aminomethyl)phenyl)-N-(4-cyclopropyl-2-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

ID: ALA4875350

PubChem CID: 164625932

Max Phase: Preclinical

Molecular Formula: C21H18F4N4O

Molecular Weight: 418.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCc1cccc(-n2nc(C(F)(F)F)cc2C(=O)Nc2ccc(C3CC3)cc2F)c1

Standard InChI:  InChI=1S/C21H18F4N4O/c22-16-9-14(13-4-5-13)6-7-17(16)27-20(30)18-10-19(21(23,24)25)28-29(18)15-3-1-2-12(8-15)11-26/h1-3,6-10,13H,4-5,11,26H2,(H,27,30)

Standard InChI Key:  KWKRSBLELBGGSQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.8372  -21.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8360  -22.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5441  -23.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2537  -22.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2509  -21.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5423  -21.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9621  -23.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6692  -22.6705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5399  -20.6276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1937  -20.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9388  -19.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1216  -19.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8715  -20.1483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6392  -18.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9693  -17.9631    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8268  -18.7986    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.0544  -18.1268    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9723  -20.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1466  -21.1909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5765  -19.8424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3551  -20.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5262  -20.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3039  -21.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9091  -20.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7313  -19.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9538  -19.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6850  -20.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7754  -18.7412    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.2330  -21.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4785  -20.6531    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
 29 27  1  0
 30 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875350

   ---

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: 418.39

Molecular Weight (Monoisotopic): 418.1417

AlogP: 4.62

#Rotatable Bonds: 5

Polar Surface Area: 72.94

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.50

CX Basic pKa: 9.25

CX LogP: 4.38

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -1.69

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