(Z)-1-(3-chloro-4-methylphenyl)-4-((6-nitrobenzo[d][1,3]dioxol-5-yl)methylene)pyrazolidine-3,5-dione

ID: ALA5289470

Max Phase: Preclinical

Molecular Formula: C18H12ClN3O6

Molecular Weight: 401.76

Names and Identifiers

Canonical SMILES:  Cc1ccc(N2NC(=O)/C(=C/c3cc4c(cc3[N+](=O)[O-])OCO4)C2=O)cc1Cl

Standard InChI:  InChI=1S/C18H12ClN3O6/c1-9-2-3-11(6-13(9)19)21-18(24)12(17(23)20-21)4-10-5-15-16(28-8-27-15)7-14(10)22(25)26/h2-7H,8H2,1H3,(H,20,23)/b12-4-

Standard InChI Key:  RKCOYYSPCQGKNT-QCDXTXTGSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   12.4227  -28.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0901  -28.7540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7588  -28.2707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5035  -27.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6794  -27.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9875  -26.8153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5394  -28.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7086  -29.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4920  -29.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1068  -29.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9330  -28.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1499  -27.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6378  -28.5228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1943  -26.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5295  -26.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3479  -25.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3736  -24.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0420  -25.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8914  -29.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6619  -30.3969    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2173  -25.4947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8859  -26.2503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7287  -24.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1979  -24.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6839  -25.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4688  -24.9725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4678  -24.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6823  -23.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
  1 13  2  0
  5 14  2  0
 14 15  1  0
 15 16  2  0
 16 25  1  0
 24 17  1  0
 17 18  2  0
 18 15  1  0
 10 19  1  0
  9 20  1  0
 21 22  2  0
 21 23  1  0
 18 21  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5289470

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 401.76

Molecular Weight (Monoisotopic): 401.0415

AlogP: 2.75

#Rotatable Bonds: 3

Polar Surface Area: 111.01

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.49

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -1.54

References

1. Goeckeler-Fried JL, Aldrin Denny R, Joshi D, Hill C, Larsen MB, Chiang AN, Frizzell RA, Wipf P, Sorscher EJ, Brodsky JL..  (2021)  Improved correction of F508del-CFTR biogenesis with a folding facilitator and an inhibitor of protein ubiquitination.,  48  [PMID:34246753] [10.1016/j.bmcl.2021.128243]

Source

Source(1):

• Scientific Literature