1-Ethenyl-6,8-difluoro-7-(4-bromo-piperidinyl)-4(1H)-oxoquinoline-3-carboxylic acid

ID: ALA1631377

PubChem CID: 50907734

Max Phase: Preclinical

Molecular Formula: C17H17BrF2N2O3

Molecular Weight: 415.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCC(Br)CC3)c(F)c21

Standard InChI:  InChI=1S/C17H17BrF2N2O3/c1-2-21-8-11(17(24)25)16(23)10-7-12(19)15(13(20)14(10)21)22-5-3-9(18)4-6-22/h7-9H,2-6H2,1H3,(H,24,25)

Standard InChI Key:  WHDQXUQCKNTJJP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.9440  -23.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9428  -24.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6576  -24.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6558  -23.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3711  -23.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3719  -24.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0871  -24.8116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8021  -24.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7974  -23.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815  -23.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2294  -23.1652    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2280  -24.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6595  -25.6426    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0771  -22.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5092  -23.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2262  -23.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5042  -22.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0888  -25.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042  -26.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177  -24.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8051  -24.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002  -25.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141  -26.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2329  -25.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0839  -26.0421    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  5  6  1  0
  3 13  1  0
  3  6  2  0
 10 14  2  0
  6  7  1  0
  9 15  1  0
  1  2  2  0
 15 16  1  0
  7  8  1  0
 15 17  2  0
  5  4  2  0
  7 18  1  0
  8  9  2  0
 18 19  1  0
 12 20  1  0
  4  1  1  0
  9 10  1  0
 10  5  1  0
  1 11  1  0
 12 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  2  3  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1631377

   7-(4-Bromo-1-piperidyl)-1-ethyl-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid

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: 415.23

Molecular Weight (Monoisotopic): 414.0391

AlogP: 3.36

#Rotatable Bonds: 3

Polar Surface Area: 62.54

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.76

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 1.33

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -0.55

References

1. Srinivasan S, Beema Shafreen RM, Nithyanand P, Manisankar P, Pandian SK..  (2010)  Synthesis and in vitro antimicrobial evaluation of novel fluoroquinolone derivatives.,  45  (12): [PMID:20933306] [10.1016/j.ejmech.2010.09.036]

Source

Source(1):

• Scientific Literature