3-((4-(Aminomethyl)-6-(trifluoromethyl)pyridin-2-yl)oxy)-N-(benzo[b]thiophen-2-ylmethyl)benzamide Hydrochloride

ID: ALA4068580

PubChem CID: 132253175

Max Phase: Preclinical

Molecular Formula: C23H19ClF3N3O2S

Molecular Weight: 457.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCc1cc(Oc2cccc(C(=O)NCc3cc4ccccc4s3)c2)nc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C23H18F3N3O2S.ClH/c24-23(25,26)20-8-14(12-27)9-21(29-20)31-17-6-3-5-16(10-17)22(30)28-13-18-11-15-4-1-2-7-19(15)32-18;/h1-11H,12-13,27H2,(H,28,30);1H

Standard InChI Key:  ATVYUGGFTFHRQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   10.1494   -2.5948    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6776   -1.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6765   -2.3820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3919   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1047   -2.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1019   -1.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3901   -1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8154   -1.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320   -1.5457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3917   -3.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6765   -4.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9650   -3.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2503   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2496   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9696   -5.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6814   -4.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9723   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586   -6.5065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6887   -6.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2613   -7.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5476   -7.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -7.4186    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665   -8.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600   -8.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -8.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4294   -8.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159   -8.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340   -9.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -9.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9624   -1.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9622   -0.3152    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2475   -1.5550    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2445   -0.7297    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 25  1  0
 24 23  1  0
 23 21  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  2 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

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: 457.48

Molecular Weight (Monoisotopic): 457.1072

AlogP: 5.50

#Rotatable Bonds: 6

Polar Surface Area: 77.24

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.84

CX LogP: 5.05

CX LogD: 3.60

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -1.71

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]

2.  (2017)  Fluorinated lysyl oxidase-like 2 inhibitors and uses thereof, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data