Racemic-trans-(3-((4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)(3-fluoro-4-hydroxypyrrolidin-1-yl)methanone Hydrochloride

ID: ALA4079398

PubChem CID: 132253084

Max Phase: Preclinical

Molecular Formula: C18H18ClF4N3O3

Molecular Weight: 399.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCc1cc(Oc2cccc(C(=O)N3C[C@@H](O)[C@H](F)C3)c2)nc(C(F)(F)F)c1

Standard InChI:  InChI=1S/C18H17F4N3O3.ClH/c19-13-8-25(9-14(13)26)17(27)11-2-1-3-12(6-11)28-16-5-10(7-23)4-15(24-16)18(20,21)22;/h1-6,13-14,26H,7-9,23H2;1H/t13-,14-;/m1./s1

Standard InChI Key:  WCLUQDIEECAJLM-DTPOWOMPSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   28.8716   -3.2189    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.8450   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8438   -2.5774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5587   -2.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2751   -2.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2722   -1.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5569   -1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9852   -1.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7012   -1.7410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5585   -3.8153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8439   -4.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1329   -3.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4189   -4.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4182   -5.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1376   -5.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8487   -5.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1304   -1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1302   -0.5127    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.4160   -1.7503    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.4130   -0.9250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.1403   -6.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4272   -6.7018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8561   -6.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6733   -6.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1233   -6.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5382   -7.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3446   -7.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3025   -6.9025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2052   -8.4540    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
  2 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 15 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 22  1  0
 25 28  1  6
 26 29  1  1
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: 399.34

Molecular Weight (Monoisotopic): 399.1206

AlogP: 2.51

#Rotatable Bonds: 4

Polar Surface Area: 88.68

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: 8.84

CX LogP: 2.00

CX LogD: 0.55

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: -1.17

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.  (2018)  Crystalline forms of a lysyl oxidase-like 2 inhibitor and methods of making, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data