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

ID: ALA353607

PubChem CID: 484067

Max Phase: Preclinical

Molecular Formula: C20H20FN3O3

Molecular Weight: 369.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(C(=O)O)c(=O)c2cc3cc(F)c(NC4CCCCC4)cc3nc21

Standard InChI:  InChI=1S/C20H20FN3O3/c1-24-10-14(20(26)27)18(25)13-7-11-8-15(21)17(9-16(11)23-19(13)24)22-12-5-3-2-4-6-12/h7-10,12,22H,2-6H2,1H3,(H,26,27)

Standard InChI Key:  KGHFRVZGMZYRAN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.5167   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -3.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -3.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -0.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -0.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -1.5500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9417   -1.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -4.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -5.6625    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  2  2  0
  9  7  1  0
 10  1  1  0
 11 13  1  0
 12  8  1  0
 13  9  2  0
 14 16  1  0
 15 11  1  0
 16 12  2  0
 17  4  2  0
 18 10  2  0
 19 14  1  0
 20 10  1  0
 21  5  1  0
 22 15  1  0
 23 22  1  0
 24 22  1  0
 25 24  1  0
 26 23  1  0
 27 25  1  0
  3  2  1  0
  9 12  1  0
 11 14  2  0
 27 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA353607

   8-(Cyclohexylamino)-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: 369.40

Molecular Weight (Monoisotopic): 369.1489

AlogP: 3.67

#Rotatable Bonds: 3

Polar Surface Area: 84.22

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.73

CX Basic pKa: 4.51

CX LogP: 3.33

CX LogD: 1.83

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -0.92

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