N1-(4-(5-fluorobenzo[b]thiophen-3-yl)benzyl)-N3-(quinolin-4-yl)propane-1,3-diamine

ID: ALA4215123

PubChem CID: 145973006

Max Phase: Preclinical

Molecular Formula: C27H24FN3S

Molecular Weight: 441.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc2scc(-c3ccc(CNCCCNc4ccnc5ccccc45)cc3)c2c1

Standard InChI:  InChI=1S/C27H24FN3S/c28-21-10-11-27-23(16-21)24(18-32-27)20-8-6-19(7-9-20)17-29-13-3-14-30-26-12-15-31-25-5-2-1-4-22(25)26/h1-2,4-12,15-16,18,29H,3,13-14,17H2,(H,30,31)

Standard InChI Key:  ODYXURFGZZRYKZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   17.4290  -22.6116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1428  -22.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1400  -21.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4272  -20.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7168  -22.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7191  -21.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0091  -20.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2962  -21.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2979  -22.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0086  -22.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4237  -20.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1338  -19.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8474  -20.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5575  -19.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2669  -20.1326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9770  -19.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6906  -20.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6893  -20.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4021  -21.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1131  -20.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1070  -20.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3937  -19.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8273  -21.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9207  -22.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7251  -22.3298    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.5795  -21.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1265  -21.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9241  -21.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1760  -20.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6199  -20.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8243  -20.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8655  -19.2721    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 27  1  0
 26 23  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4215123

   ---

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: 441.58

Molecular Weight (Monoisotopic): 441.1675

AlogP: 6.85

#Rotatable Bonds: 8

Polar Surface Area: 36.95

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.28

CX LogP: 5.69

CX LogD: 3.13

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.26

Np Likeness Score: -1.45

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