1-cyclopropyl-6-fluoro-7-(1H-isoindol-2(3H,3aH,4H,5H,6H,7H,7aH)-yl)-8-methoxy-3-(thiazolidine-3-carbonyl)quinolin-4(1H)-one

ID: ALA4637080

PubChem CID: 156012186

Max Phase: Preclinical

Molecular Formula: C25H30FN3O3S

Molecular Weight: 471.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(N2CC3CCCCC3C2)c(F)cc2c(=O)c(C(=O)N3CCSC3)cn(C3CC3)c12

Standard InChI:  InChI=1S/C25H30FN3O3S/c1-32-24-21-18(10-20(26)22(24)28-11-15-4-2-3-5-16(15)12-28)23(30)19(13-29(21)17-6-7-17)25(31)27-8-9-33-14-27/h10,13,15-17H,2-9,11-12,14H2,1H3

Standard InChI Key:  AMFNITZIRFYQBM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
   23.5403   -2.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5392   -3.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2472   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2454   -2.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9540   -2.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9528   -3.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6629   -4.2086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3788   -3.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3800   -2.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6653   -2.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6653   -1.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0887   -2.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0907   -1.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8325   -2.5673    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.6606   -5.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7954   -2.9776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2538   -5.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0710   -5.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8760   -3.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6750   -3.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0853   -3.2530    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.5399   -2.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2469   -5.0214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5390   -5.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8357   -4.2024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0894   -3.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7496   -5.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9502   -5.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5431   -4.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7285   -4.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3148   -5.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7218   -5.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5426   -5.8923    0.0000 C   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
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  2  0
  1 14  1  0
  7 15  1  0
 12 16  1  0
 17 15  1  0
 18 17  1  0
 15 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 16  1  0
  3 23  1  0
 23 24  1  0
 25 26  1  0
 26 29  1  0
 28 27  1  0
 27 25  1  0
  2 25  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4637080

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 471.60

Molecular Weight (Monoisotopic): 471.1992

AlogP: 4.26

#Rotatable Bonds: 4

Polar Surface Area: 54.78

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.40

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.67

Np Likeness Score: -0.74

References

1. 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]

2. Dighe SN, Collet TA..  (2020)  Recent advances in DNA gyrase-targeted antimicrobial agents.,  199  [PMID:32460040] [10.1016/j.ejmech.2020.112326]

Source

Source(1):

• Scientific Literature