2-(3,5-difluorophenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)acetamide

ID: ALA4875991

PubChem CID: 164626356

Max Phase: Preclinical

Molecular Formula: C21H22F5N3O

Molecular Weight: 427.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1CCN(c2nc(C(F)(F)F)ccc2CNC(=O)Cc2cc(F)cc(F)c2)CC1

Standard InChI:  InChI=1S/C21H22F5N3O/c1-13-4-6-29(7-5-13)20-15(2-3-18(28-20)21(24,25)26)12-27-19(30)10-14-8-16(22)11-17(23)9-14/h2-3,8-9,11,13H,4-7,10,12H2,1H3,(H,27,30)

Standard InChI Key:  NWFBPKBPOKYCMH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.3979  -16.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3967  -17.6893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1115  -18.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8279  -17.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8251  -16.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1097  -16.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6833  -16.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6831  -15.6246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.9690  -16.8623    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.9660  -16.0370    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.1113  -18.9270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3955  -19.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3933  -20.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1058  -20.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8222  -20.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8260  -19.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1025  -21.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5430  -18.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2568  -17.6865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9720  -18.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6857  -17.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9732  -18.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4008  -18.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3977  -18.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1120  -19.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8267  -18.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8228  -18.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1079  -17.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5351  -17.6736    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.1129  -20.1576    0.0000 F   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
 27 29  1  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875991

   ---

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: 427.42

Molecular Weight (Monoisotopic): 427.1683

AlogP: 4.47

#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: 13.81

CX Basic pKa: 2.51

CX LogP: 4.92

CX LogD: 4.92

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.72

Np Likeness Score: -1.64

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