1-Ethyl-6-fluoro-7-(4-(2-hydroxy-6-methylbenzoyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA3770650

PubChem CID: 122387507

Max Phase: Preclinical

Molecular Formula: C24H24FN3O5

Molecular Weight: 453.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C(=O)c4c(C)cccc4O)CC3)cc21

Standard InChI:  InChI=1S/C24H24FN3O5/c1-3-26-13-16(24(32)33)22(30)15-11-17(25)19(12-18(15)26)27-7-9-28(10-8-27)23(31)21-14(2)5-4-6-20(21)29/h4-6,11-13,29H,3,7-10H2,1-2H3,(H,32,33)

Standard InChI Key:  DJXXWZURDKMNHY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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
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    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
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   -4.9506   -0.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8951    2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0931    2.9862    0.0000 C   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
   11.6912    2.9730    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
   10.3808    0.7296    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
    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
   10.4021    4.9295    0.0000 O   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
    8.0434    0.8914    0.0000 C   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
 23 30  1  0
  1 31  1  0
 31 32  1  0
 27 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3770650

   ---

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: 453.47

Molecular Weight (Monoisotopic): 453.1700

AlogP: 2.84

#Rotatable Bonds: 4

Polar Surface Area: 103.08

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.88

CX Basic pKa: 0.01

CX LogP: 3.77

CX LogD: 2.19

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.63

Np Likeness Score: -1.02

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