8-Azocan-1-yl-7-fluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

ID: ALA170915

PubChem CID: 484068

Max Phase: Preclinical

Molecular Formula: C21H22FN3O3

Molecular Weight: 383.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C(=O)O)c(=O)c2cc3cc(F)c(N4CCCCCCC4)cc3nc21

Standard InChI:  InChI=1S/C21H22FN3O3/c1-24-12-15(21(27)28)19(26)14-9-13-10-16(22)18(11-17(13)23-20(14)24)25-7-5-3-2-4-6-8-25/h9-12H,2-8H2,1H3,(H,27,28)

Standard InChI Key:  NMGBTIAUEHMVMI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    6.9625   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -1.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -1.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625   -1.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417    0.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875    0.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    0.0708    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -0.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  1  1  0
  5  6  1  0
  6  1  2  0
  7  3  2  0
  8 11  1  0
  9  7  1  0
 10  2  2  0
 11  9  2  0
 12  1  1  0
 13 10  1  0
 14  8  1  0
 15 16  1  0
 16 13  2  0
 17  4  2  0
 18 12  2  0
 19 15  1  0
 20 12  1  0
 21  5  1  0
 22 14  1  0
 23 14  1  0
 24 22  1  0
 25 23  1  0
 26 24  1  0
 27 25  1  0
 28 27  1  0
  3  2  1  0
  9 13  1  0
  8 15  2  0
 28 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA170915

   8-(Azocan-1-yl)-7-fluoro-1-methyl-4-oxo-benzo[b][1,8]naphthyridine-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: 383.42

Molecular Weight (Monoisotopic): 383.1645

AlogP: 3.69

#Rotatable Bonds: 2

Polar Surface Area: 75.43

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.72

CX Basic pKa: 4.45

CX LogP: 3.92

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -0.91

References

1. Tabart M, Picaut G, Desconclois JF, Dutka-Malen S, Huet Y, Berthaud N..  (2001)  Synthesis and biological evaluation of benzo[b]naphthyridones, a series of new topical antibacterial agents.,  11  (7): [PMID:11294391] [10.1016/s0960-894x(01)00091-9]

Source

Source(1):

• Scientific Literature