7-[(4-(Dimethylamino)methyl)phenoxy)methyl]quinolin-2-amine dihydrochloride

ID: ALA3736445

PubChem CID: 127034910

Max Phase: Preclinical

Molecular Formula: C19H23Cl2N3O

Molecular Weight: 307.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1ccc(OCc2ccc3ccc(N)nc3c2)cc1.Cl.Cl

Standard InChI:  InChI=1S/C19H21N3O.2ClH/c1-22(2)12-14-4-8-17(9-5-14)23-13-15-3-6-16-7-10-19(20)21-18(16)11-15;;/h3-11H,12-13H2,1-2H3,(H2,20,21);2*1H

Standard InChI Key:  HAQSFXWPRNSFLH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    6.3926    2.2514    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    1.3486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    0.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8113    0.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1103    1.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1101    2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8110    3.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    2.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4083    3.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4060    5.2468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4439    5.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3656    5.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8926    2.2514    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  6  2  0
 10 12  1  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  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: 307.40

Molecular Weight (Monoisotopic): 307.1685

AlogP: 3.46

#Rotatable Bonds: 5

Polar Surface Area: 51.38

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.74

CX LogP: 3.40

CX LogD: 2.04

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.78

Np Likeness Score: -0.81

References

1. Cinelli MA, Li H, Pensa AV, Kang S, Roman LJ, Martásek P, Poulos TL, Silverman RB..  (2015)  Phenyl Ether- and Aniline-Containing 2-Aminoquinolines as Potent and Selective Inhibitors of Neuronal Nitric Oxide Synthase.,  58  (21): [PMID:26469213] [10.1021/acs.jmedchem.5b01330]

Source

Source(1):

• Scientific Literature