7-(3-Amino-pyrrolidin-1-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid hydrochloride

ID: ALA542832

Cas Number: 104051-69-6

PubChem CID: 10433396

Max Phase: Preclinical

Molecular Formula: C19H16ClF3N4O3

Molecular Weight: 404.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NC1CCN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2F)C1

Standard InChI:  InChI=1S/C19H15F3N4O3.ClH/c20-9-1-2-15(13(21)5-9)26-8-12(19(28)29)16(27)11-6-14(22)18(24-17(11)26)25-4-3-10(23)7-25;/h1-2,5-6,8,10H,3-4,7,23H2,(H,28,29);1H

Standard InChI Key:  CIHZSSCESOLBRQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    6.2322    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2767    0.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -0.0609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2767    1.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056    1.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378   -0.0609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    1.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056    0.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523    0.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668   -0.0609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -0.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378    1.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4201    1.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523    1.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2767   -1.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2767   -2.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056   -1.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6204    0.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530   -0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    2.4141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    1.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7600   -1.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -2.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668    1.5891    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378   -0.8859    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4201    2.4141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056   -2.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9929   -0.2522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911   -3.3609    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  2  0
  2  6  1  0
  4  7  1  0
  5  7  1  0
  3  8  1  0
  5  8  2  0
  6  9  2  0
  9 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  9 14  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 11 17  2  0
 10 18  1  0
 10 19  1  0
  7 20  2  0
 13 21  2  0
 19 22  1  0
 16 23  1  0
 14 24  1  0
 15 25  1  0
 18 26  1  0
 22 26  1  0
 13 27  1  0
 17 28  1  0
 23 28  2  0
 26 29  1  0
 23 30  1  0
M  END

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: 404.35

Molecular Weight (Monoisotopic): 404.1096

AlogP: 2.04

#Rotatable Bonds: 3

Polar Surface Area: 101.45

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.22

CX Basic pKa: 9.63

CX LogP: 0.47

CX LogD: 0.47

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -1.05

References

1. Rosen T, Chu DT, Lico IM, Fernandes PB, Shen L, Borodkin S, Pernet AG..  (1988)  Asymmetric synthesis and properties of the enantiomers of the antibacterial agent 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-1,4-dihydro-6- fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride.,  31  (8): [PMID:3397996] [10.1021/jm00403a017]

2. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

Source

Source(2):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21