6-chloro-2-((4-fluorophenyl)amino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA5285950

Max Phase: Preclinical

Molecular Formula: C16H10ClFN2O3

Molecular Weight: 332.72

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(Nc2ccc(F)cc2)[nH]c2ccc(Cl)cc2c1=O

Standard InChI:  InChI=1S/C16H10ClFN2O3/c17-8-1-6-12-11(7-8)14(21)13(16(22)23)15(20-12)19-10-4-2-9(18)3-5-10/h1-7H,(H,22,23)(H2,19,20,21)

Standard InChI Key:  FYSJJCXDPRZXNO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -1.7851    1.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    2.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    0.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559    2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559    0.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559    2.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    2.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    1.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851   -0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989   -1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675   -0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    2.0615    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -2.8870    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  7 11  2  0
  8 12  1  0
 12 13  2  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 16 21  1  0
  1 22  1  0
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285950

   ---

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: 332.72

Molecular Weight (Monoisotopic): 332.0364

AlogP: 3.76

#Rotatable Bonds: 3

Polar Surface Area: 82.19

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.71

CX Basic pKa: 0.24

CX LogP: 3.85

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.97

References

1. Shin YS, Lee JY, Jeon S, Myung S, Gong HJ, Kim S, Kim HR, Jeong LS, Park CM..  (2023)  Discovery of 2-aminoquinolone acid derivatives as potent inhibitors of SARS-CoV-2.,  85  [PMID:36870624] [10.1016/j.bmcl.2023.129214]

Source

Source(1):

• Scientific Literature