2-(2-chlorophenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)acetamide

ID: ALA4878230

PubChem CID: 164628300

Max Phase: Preclinical

Molecular Formula: C21H23ClF3N3O

Molecular Weight: 425.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1CCN(c2nc(C(F)(F)F)ccc2CNC(=O)Cc2ccccc2Cl)CC1

Standard InChI:  InChI=1S/C21H23ClF3N3O/c1-14-8-10-28(11-9-14)20-16(6-7-18(27-20)21(23,24)25)13-26-19(29)12-15-4-2-3-5-17(15)22/h2-7,14H,8-13H2,1H3,(H,26,29)

Standard InChI Key:  WDKUMDGQNWQCDA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   38.4105   -2.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4094   -2.8606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.1241   -3.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8406   -2.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8377   -2.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1223   -1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6959   -1.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6957   -0.7959    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.9816   -2.0336    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.9786   -1.2083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   39.1239   -4.0984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4081   -4.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4059   -5.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1185   -5.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8348   -5.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8387   -4.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1151   -6.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5556   -3.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2695   -2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9845   -3.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6984   -2.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9859   -4.0943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.4135   -3.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4103   -4.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1246   -4.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8394   -4.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8355   -3.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1206   -2.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1161   -2.0286    0.0000 Cl  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
  1  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  3 11  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
  4 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878230

   ---

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: 425.88

Molecular Weight (Monoisotopic): 425.1482

AlogP: 4.85

#Rotatable Bonds: 5

Polar Surface Area: 45.23

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.51

CX LogP: 5.24

CX LogD: 5.24

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: -1.79

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