N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluorophenyl)acetamide

ID: ALA4876653

PubChem CID: 49802518

Max Phase: Preclinical

Molecular Formula: C22H23ClFN3O

Molecular Weight: 399.90

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(CNC(=O)Cc2cccc(F)c2)n(-c2cccc(Cl)c2)n1

Standard InChI:  InChI=1S/C22H23ClFN3O/c1-22(2,3)20-13-19(27(26-20)18-9-5-7-16(23)12-18)14-25-21(28)11-15-6-4-8-17(24)10-15/h4-10,12-13H,11,14H2,1-3H3,(H,25,28)

Standard InChI Key:  HZJKAPMSEWIGJK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   29.7817  -13.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6044  -14.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2148  -14.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0029  -14.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1770  -13.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5651  -13.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6139  -15.0108    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.7385  -12.2858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4872  -11.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4028  -11.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5962  -10.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1822  -11.6694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2019  -12.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9161  -11.9492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6308  -12.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3450  -11.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6311  -13.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0597  -12.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0569  -13.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7707  -13.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4859  -13.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4830  -12.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7687  -11.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1958  -11.9390    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.2623  -10.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7486   -9.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4419  -10.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8451   -9.4832    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
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 22 24  1  0
 11 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876653

   N-[[5-tert-butyl-2-(3-chlorophenyl)pyrazol-3-yl]methyl]-2-(3-fluorophenyl)acetamide

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: 399.90

Molecular Weight (Monoisotopic): 399.1514

AlogP: 4.82

#Rotatable Bonds: 5

Polar Surface Area: 46.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.52

CX Basic pKa: 2.02

CX LogP: 5.44

CX LogD: 5.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -1.99

References

1. Kang JM, Kwon SO, Ann J, Lee S, Kim C, Do N, Jeong JJ, Blumberg PM, Ha H, Vu TNL, Yoon S, Choi S, Frank-Foltyn R, Lesch B, Bahrenberg G, Stockhausen H, Christoph T, Lee J..  (2021)  2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists.,  48  [PMID:34273488] [10.1016/j.bmcl.2021.128266]

Source

Source(1):

• Scientific Literature