N-(4-acetamidophenyl)-8-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide

ID: ALA5280296

Max Phase: Preclinical

Molecular Formula: C18H14ClN3O3

Molecular Weight: 355.78

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccc(NC(=O)c2c[nH]c3c(Cl)cccc3c2=O)cc1

Standard InChI:  InChI=1S/C18H14ClN3O3/c1-10(23)21-11-5-7-12(8-6-11)22-18(25)14-9-20-16-13(17(14)24)3-2-4-15(16)19/h2-9H,1H3,(H,20,24)(H,21,23)(H,22,25)

Standard InChI Key:  HIJMQKFRILEBDM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.5038   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7832    0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7709    1.0524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750   -0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538   -0.2169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    0.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5033    0.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5156    0.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867    1.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3420    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078   -1.4224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161   -0.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2368   -1.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9451   -0.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9328   -0.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2121    0.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2368   -2.2264    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2304    1.4011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9451    0.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450    0.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595    1.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  4  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 12  7  2  0
 11 12  1  0
  5 13  2  0
 14  4  2  0
 15 14  1  0
 16 15  1  0
  1 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20  1  2  0
 17 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280296

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.78

Molecular Weight (Monoisotopic): 355.0724

AlogP: 3.39

#Rotatable Bonds: 3

Polar Surface Area: 91.06

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.10

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -1.11

References

1. Chen X, Zhu H, Liu X, Li Q, Dong M..  (2023)  Design and synthesis of novel GluN2A NMDAR positive allosteric modulators via scaffold hopping strategy as anti-stroke therapeutic agents.,  83  [PMID:36934527] [10.1016/j.bmc.2023.117236]

Source

Source(1):

• Scientific Literature