(E)-N-(7-chloroquinolin-4-yl)-3-(2-nitrophenyl)acrylamide

ID: ALA2042198

PubChem CID: 66573734

Max Phase: Preclinical

Molecular Formula: C18H12ClN3O3

Molecular Weight: 353.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1[N+](=O)[O-])Nc1ccnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C18H12ClN3O3/c19-13-6-7-14-15(9-10-20-16(14)11-13)21-18(23)8-5-12-3-1-2-4-17(12)22(24)25/h1-11H,(H,20,21,23)/b8-5+

Standard InChI Key:  DINDEPNPTTUNSU-VMPITWQZSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -0.0180    1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    0.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4109    1.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253    1.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    0.6281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1289    0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1361   -0.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -0.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650   -0.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5578    0.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8397    1.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -0.5906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4325   -1.4156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7072   -0.1844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7072   -1.8468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0036   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036   -0.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217   -0.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4325   -0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1505   -0.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614   -0.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542   -1.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361   -1.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -1.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650   -1.8718    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  2  0
 12 14  1  0
  7 12  1  0
  3  6  1  0
 15 16  2  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 23  1  0
 23 24  2  0
 15 24  1  0
 19 24  1  0
 22 25  1  0
  5 18  1  0
M  CHG  2  12   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2042198

   (E)-N-(7-chloro-4-quinolyl)-3-(2-nitrophenyl)prop-2-enamide

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: 353.77

Molecular Weight (Monoisotopic): 353.0567

AlogP: 4.45

#Rotatable Bonds: 4

Polar Surface Area: 85.13

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.45

CX Basic pKa: 4.21

CX LogP: 4.27

CX LogD: 4.27

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -1.53

References

1. Pérez BC, Teixeira C, Figueiras M, Gut J, Rosenthal PJ, Gomes JR, Gomes P..  (2012)  Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: towards the development of potential dual action antimalarials.,  54  [PMID:22683112] [10.1016/j.ejmech.2012.05.022]

Source

Source(1):

• Scientific Literature