7-[((5-((Methylamino)methyl)pyridin-3-yl)oxy)methyl]quinolin-2-amine trihydrochloride

ID: ALA3736490

PubChem CID: 127034913

Max Phase: Preclinical

Molecular Formula: C17H21Cl3N4O

Molecular Weight: 294.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCc1cncc(OCc2ccc3ccc(N)nc3c2)c1.Cl.Cl.Cl

Standard InChI:  InChI=1S/C17H18N4O.3ClH/c1-19-8-13-6-15(10-20-9-13)22-11-12-2-3-14-4-5-17(18)21-16(14)7-12;;;/h2-7,9-10,19H,8,11H2,1H3,(H2,18,21);3*1H

Standard InChI Key:  RDBIEICONZKFIZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 24  0  0  0  0  0  0  0  0999 V2000
    6.3926    2.9977    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 N   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
   -7.8078    5.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5069    5.9918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5043    7.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3926    2.9977    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8926    2.9977    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
 19 21  1  0
 21 22  1  0
 22 23  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: 294.36

Molecular Weight (Monoisotopic): 294.1481

AlogP: 2.51

#Rotatable Bonds: 5

Polar Surface Area: 73.06

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 1.80

CX LogD: 0.39

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: -0.52

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