Dimethyl-{2-[3-(4-propoxy-phenyl)-quinolin-2-ylsulfanyl]-ethyl}-amine hydrochloride

ID: ALA541554

PubChem CID: 13200254

Max Phase: Preclinical

Molecular Formula: C22H27ClN2OS

Molecular Weight: 366.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1ccc(-c2cc3ccccc3nc2SCCN(C)C)cc1.Cl

Standard InChI:  InChI=1S/C22H26N2OS.ClH/c1-4-14-25-19-11-9-17(10-12-19)20-16-18-7-5-6-8-21(18)23-22(20)26-15-13-24(2)3;/h5-12,16H,4,13-15H2,1-3H3;1H

Standard InChI Key:  QKHGAVPSMAIURI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    5.0929    1.1291    0.0000 Cl  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 N   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
   -3.9086   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -0.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025    5.2568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5078   -3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2093   -3.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9067    3.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8096   -3.7478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049    3.7560    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
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2404    5.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1622    5.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1077   -2.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4096   -3.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4475   -3.1392    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
  2  3  2  0
  2  4  1  0
  4  5  2  0
  3  6  1  0
  5  7  1  0
  6  7  1  0
  4  8  1  0
  2  9  1  0
  8 10  1  0
  8 11  2  0
 10 14  2  0
 13 14  1  0
 11 15  1  0
 13 15  2  0
  9 16  1  0
 13 17  1  0
 12 18  1  0
 16 18  1  0
  6 19  2  0
  7 20  2  0
 12 21  1  0
 12 22  1  0
 17 23  1  0
 23 24  1  0
 24 25  1  0
 19 26  1  0
 20 27  1  0
 26 27  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: 366.53

Molecular Weight (Monoisotopic): 366.1766

AlogP: 5.34

#Rotatable Bonds: 8

Polar Surface Area: 25.36

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.47

CX LogP: 5.48

CX LogD: 4.38

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.50

Np Likeness Score: -1.12

References

1. Blackburn TP, Cox B, Guildford AJ, Le Count DJ, Middlemiss DN, Pearce RJ, Thornber CW..  (1987)  Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogues.,  30  (12): [PMID:3681895] [10.1021/jm00395a013]

Source

Source(1):

• Scientific Literature