(S)-3-((4-(Aminomethyl)-6-(trifluoromethyl)pyridin-2-yl)oxy)-Nphenylpiperidine-1-carboxamide Hydrochloride

ID: ALA4087273

PubChem CID: 122517043

Max Phase: Preclinical

Molecular Formula: C19H21F3N4O2

Molecular Weight: 394.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCc1cc(O[C@H]2CCCN(C(=O)Nc3ccccc3)C2)nc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C19H21F3N4O2/c20-19(21,22)16-9-13(11-23)10-17(25-16)28-15-7-4-8-26(12-15)18(27)24-14-5-2-1-3-6-14/h1-3,5-6,9-10,15H,4,7-8,11-12,23H2,(H,24,27)/t15-/m0/s1

Standard InChI Key:  NPNATZWDBSJWKE-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   16.3514  -11.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3501  -11.9346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0650  -12.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7813  -11.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7784  -11.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0632  -10.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4914  -10.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2072  -11.0983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0648  -13.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6368  -10.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6367   -9.8701    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9224  -11.1077    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9195  -10.2824    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.3501  -13.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6354  -13.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9230  -13.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9185  -14.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6328  -14.8162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3513  -14.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6297  -15.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9138  -16.0510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3426  -16.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2009  -15.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2088  -14.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4967  -14.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7798  -14.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7795  -15.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4920  -16.0494    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
  5  7  1  0
  7  8  1  0
  3  9  1  0
  1 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 14  9  1  6
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 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
M  END

Alternative Forms

1. Parent:

   

   ALA4087273

   ---

2. Alternative Forms:

   

   ALA4087273

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.40

Molecular Weight (Monoisotopic): 394.1617

AlogP: 3.63

#Rotatable Bonds: 4

Polar Surface Area: 80.48

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.41

CX Basic pKa: 8.87

CX LogP: 3.20

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.83

Np Likeness Score: -1.49

References

1. Rowbottom MW, Bain G, Calderon I, Lasof T, Lonergan D, Lai A, Huang F, Darlington J, Prodanovich P, Santini AM, King CD, Goulet L, Shannon KE, Ma GL, Nguyen K, MacKenna DA, Evans JF, Hutchinson JH..  (2017)  Identification of 4-(Aminomethyl)-6-(trifluoromethyl)-2-(phenoxy)pyridine Derivatives as Potent, Selective, and Orally Efficacious Inhibitors of the Copper-Dependent Amine Oxidase, Lysyl Oxidase-Like 2 (LOXL2).,  60  (10): [PMID:28471663] [10.1021/acs.jmedchem.7b00345]

Source

Source(1):

• Scientific Literature