7-(4-(2-Chloronicotinoyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA3770164

PubChem CID: 122387497

Max Phase: Preclinical

Molecular Formula: C22H20ClFN4O4

Molecular Weight: 458.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C(=O)c4cccnc4Cl)CC3)cc21

Standard InChI:  InChI=1S/C22H20ClFN4O4/c1-2-26-12-15(22(31)32)19(29)14-10-16(24)18(11-17(14)26)27-6-8-28(9-7-27)21(30)13-4-3-5-25-20(13)23/h3-5,10-12H,2,6-9H2,1H3,(H,31,32)

Standard InChI Key:  YFPGPJWFJFJKRB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506   -0.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -2.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    1.4990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953    3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931    2.9949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4907    1.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7956    3.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0931    2.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0856    1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3808    0.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6836    1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6912    2.9730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3960    3.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7997    4.9405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321   -1.3486    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    3.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4021    4.9295    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
 11 12  2  0
 11 13  1  0
  3 11  1  0
  4 14  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 21 28  2  0
 18 21  1  0
  8 15  1  0
  7 29  1  0
 30 31  1  0
  1 30  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3770164

   ---

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: 458.88

Molecular Weight (Monoisotopic): 458.1157

AlogP: 2.87

#Rotatable Bonds: 4

Polar Surface Area: 95.74

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 0.67

CX LogP: 2.52

CX LogD: 0.99

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -1.49

References

1. Sha S, Han H, Gao F, Liu T, Li Z, Xu C, Zhong W, Zhu H.  (2015)  Discovery of fluoroquinolone derivatives as potent, selective inhibitors of PI3K,  6  (11): [10.1039/C5MD00364D]

Source

Source(1):

• Scientific Literature