N1-(2-Adamantan-1-yl-ethyl)-N3-(7-chloro-quinolin-4-yl)-N1-methyl-butane-1,3-diamine

ID: ALA4209247

PubChem CID: 145965174

Max Phase: Preclinical

Molecular Formula: C26H36ClN3

Molecular Weight: 426.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CCN(C)CCC12CC3CC(CC(C3)C1)C2)Nc1ccnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C26H36ClN3/c1-18(29-24-5-8-28-25-14-22(27)3-4-23(24)25)6-9-30(2)10-7-26-15-19-11-20(16-26)13-21(12-19)17-26/h3-5,8,14,18-21H,6-7,9-13,15-17H2,1-2H3,(H,28,29)

Standard InChI Key:  PTZHOZONAZPNBE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   22.2468   -8.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8820   -7.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0436   -8.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5866   -8.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7975   -8.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3315   -8.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0410   -7.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5923   -6.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8776   -7.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3414   -7.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2924  -10.9124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0021  -10.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9993   -9.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2907   -9.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5844  -10.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5867   -9.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8807   -9.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1721   -9.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1737  -10.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8803  -10.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4670  -10.9153    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.2872   -8.4579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5777   -8.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8718   -8.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5742   -7.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1623   -8.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4564   -8.4700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7469   -8.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4599   -9.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0409   -8.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 15 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 16  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  2  0
 19 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 28 30  1  0
 30  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4209247

   ---

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: 426.05

Molecular Weight (Monoisotopic): 425.2598

AlogP: 6.62

#Rotatable Bonds: 8

Polar Surface Area: 28.16

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.95

CX LogP: 5.42

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -0.78

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