3-((4-(Aminomethyl)pyridin-2-yl)oxy)-N-(3-carbamimidoylbenzyl)benzamide Dihydrochloride

ID: ALA4085053

PubChem CID: 137648233

Max Phase: Preclinical

Molecular Formula: C21H23Cl2N5O2

Molecular Weight: 375.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N=C(N)c1ccc(CNC(=O)c2cccc(Oc3cc(CN)ccn3)c2)cc1

Standard InChI:  InChI=1S/C21H21N5O2.2ClH/c22-12-15-8-9-25-19(10-15)28-18-3-1-2-17(11-18)21(27)26-13-14-4-6-16(7-5-14)20(23)24;;/h1-11H,12-13,22H2,(H3,23,24)(H,26,27);2*1H

Standard InChI Key:  RXEMTCDWKQKMAO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
   27.9519  -13.2698    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.5328   -8.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5317   -8.8815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2470   -9.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9597   -8.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9569   -8.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2452   -7.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6703   -7.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3867   -8.0452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2467  -10.1171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5317  -10.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8203  -10.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1057  -10.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1051  -11.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8249  -11.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5366  -11.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8276  -12.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1140  -13.0053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5439  -13.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3977  -12.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6841  -13.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9711  -12.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2621  -13.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2644  -13.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9815  -14.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6917  -13.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5513  -14.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8345  -13.8428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5551  -15.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2984  -10.1494    0.0000 Cl  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  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 27 28  1  0
 27 29  2  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: 375.43

Molecular Weight (Monoisotopic): 375.1695

AlogP: 2.55

#Rotatable Bonds: 7

Polar Surface Area: 127.11

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 11.48

CX LogP: 1.70

CX LogD: -2.27

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -1.16

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