4-({3-[4-(3-{[2-(1-adamantyl)ethyl]ammonio}propyl)piperazinediium-1-yl]propyl}amino)-7-chloroquinolinium tetrachloride

ID: ALA4217177

PubChem CID: 145974487

Max Phase: Preclinical

Molecular Formula: C31H50Cl5N5

Molecular Weight: 524.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.Cl.Cl.Clc1ccc2c(NCCCN3CCN(CCCNCCC45CC6CC(CC(C6)C4)C5)CC3)ccnc2c1

Standard InChI:  InChI=1S/C31H46ClN5.4ClH/c32-27-3-4-28-29(5-9-35-30(28)20-27)34-8-2-12-37-15-13-36(14-16-37)11-1-7-33-10-6-31-21-24-17-25(22-31)19-26(18-24)23-31;;;;/h3-5,9,20,24-26,33H,1-2,6-8,10-19,21-23H2,(H,34,35);4*1H

Standard InChI Key:  PJWHQHHDDWMBJO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 42  0  0  0  0  0  0  0  0999 V2000
   46.1705   -9.4580    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   40.1644   -8.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7996   -8.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9613   -8.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5042   -8.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7151   -9.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2491   -8.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9586   -7.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5099   -7.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7952   -7.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2590   -7.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.4515   -9.5669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   52.1612   -9.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.1584   -8.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.4497   -7.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.7435   -9.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.7458   -8.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.0398   -7.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.3311   -8.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.3328   -9.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.0393   -9.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.6261   -9.5699    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   51.4463   -7.1124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   50.7368   -6.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.0308   -7.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.3214   -6.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.6154   -7.1245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   47.9075   -6.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2036   -7.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2029   -7.9422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   47.9122   -8.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.6222   -7.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.4954   -8.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7875   -7.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0800   -8.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3720   -7.9436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.6645   -8.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9566   -7.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1652   -9.5759    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.2848   -9.5464    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   45.1982   -9.4580    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  7  1  0
  6  7  1  0
  8  9  1  0
  4  8  1  0
  3 10  1  0
  7 11  1  0
 11  9  1  0
  9 10  1  0
 16 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 17  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  2  0
 20 22  1  0
 15 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38  7  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: 524.20

Molecular Weight (Monoisotopic): 523.3442

AlogP: 5.89

#Rotatable Bonds: 12

Polar Surface Area: 43.43

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 10.42

CX LogP: 4.54

CX LogD: 0.83

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.34

Np Likeness Score: -0.89

References

1. Konstantinović J, Videnović M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić Jovanović N, Gradoni L, Basilico N, Šolaja BA..  (2018)  Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice.,  9  (7): [PMID:30034591] [10.1021/acsmedchemlett.8b00053]

Source

Source(1):

• Scientific Literature