7-(4-((5-(2-(4-chlorophenyl)-2-oxoethylthio)-1,3,4-oxadiazol-2-yl)methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ID: ALA4213701

PubChem CID: 145965601

Max Phase: Preclinical

Molecular Formula: C28H25ClFN5O5S

Molecular Weight: 598.06

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CSc1nnc(CN2CCN(c3cc4c(cc3F)c(=O)c(C(=O)O)cn4C3CC3)CC2)o1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C28H25ClFN5O5S/c29-17-3-1-16(2-4-17)24(36)15-41-28-32-31-25(40-28)14-33-7-9-34(10-8-33)23-12-22-19(11-21(23)30)26(37)20(27(38)39)13-35(22)18-5-6-18/h1-4,11-13,18H,5-10,14-15H2,(H,38,39)

Standard InChI Key:  SBNFVNDBLXBTIU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   26.3916  -16.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1002  -16.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0990  -17.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8091  -18.0885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5249  -17.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5261  -16.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8115  -16.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2349  -16.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9416  -16.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2369  -15.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   24.9786  -16.4471    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   23.5605  -18.8955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2678  -19.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9799  -18.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8105  -18.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3999  -19.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2171  -19.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8510  -19.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1451  -18.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0606  -18.0791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2620  -17.9056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8502  -18.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3943  -19.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0371  -18.6932    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.5597  -18.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7466  -18.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2693  -17.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4109  -18.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6088  -16.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1322  -16.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3182  -16.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9831  -16.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4618  -17.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8400  -15.4628    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
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  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
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  9 10  1  0
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  9 11  1  0
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  1 15  1  0
 16 17  1  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  2 16  1  0
 23 22  1  0
 24 23  1  0
 22 24  1  0
  7 22  1  0
 19 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 34 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 34  1  0
 38 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4213701

   ---

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: 598.06

Molecular Weight (Monoisotopic): 597.1249

AlogP: 4.51

#Rotatable Bonds: 9

Polar Surface Area: 121.77

Molecular Species: ACID

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.87

CX Basic pKa: 3.45

CX LogP: 3.55

CX LogD: 2.01

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.22

Np Likeness Score: -1.72

References

1. Kassab AE, Gedawy EM..  (2018)  Novel ciprofloxacin hybrids using biology oriented drug synthesis (BIODS) approach: Anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis, topoisomerase II inhibition, and antibacterial activity.,  150  [PMID:29547830] [10.1016/j.ejmech.2018.03.026]

2. Suaifan GARY, Mohammed AAM..  (2019)  Fluoroquinolones structural and medicinal developments (2013-2018): Where are we now?,  27  (14): [PMID:31182257] [10.1016/j.bmc.2019.05.038]

Source

Source(1):

• Scientific Literature