1-(3,4-dichlorobenzyl)-N-(methylsulfonyl)-5-oxopyrrolidine-3-carboxamide

ID: ALA4534722

PubChem CID: 155547188

Max Phase: Preclinical

Molecular Formula: C13H14Cl2N2O4S

Molecular Weight: 365.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)NC(=O)C1CC(=O)N(Cc2ccc(Cl)c(Cl)c2)C1

Standard InChI:  InChI=1S/C13H14Cl2N2O4S/c1-22(20,21)16-13(19)9-5-12(18)17(7-9)6-8-2-3-10(14)11(15)4-8/h2-4,9H,5-7H2,1H3,(H,16,19)

Standard InChI Key:  OUTITZGEANHLDY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   22.1385  -13.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5512  -13.7643    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.9596  -13.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4298  -14.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1375  -13.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8452  -14.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1375  -12.9512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2606  -14.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6814  -13.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1346  -14.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5433  -15.1639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3425  -14.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3219  -14.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2109  -15.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3982  -15.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9204  -15.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1084  -15.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7753  -16.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2603  -16.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0706  -16.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9627  -16.2541    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.9306  -17.5782    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  6  2  1  0
  2  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  4  1  0
 10 13  2  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534722

   ---

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: 365.24

Molecular Weight (Monoisotopic): 364.0051

AlogP: 1.42

#Rotatable Bonds: 4

Polar Surface Area: 83.55

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.03

CX Basic pKa: ┄

CX LogP: 0.63

CX LogD: -0.31

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.87

Np Likeness Score: -1.62

References

1. DiMauro EF, Altmann S, Berry LM, Bregman H, Chakka N, Chu-Moyer M, Bojic EF, Foti RS, Fremeau R, Gao H, Gunaydin H, Guzman-Perez A, Hall BE, Huang H, Jarosh M, Kornecook T, Lee J, Ligutti J, Liu D, Moyer BD, Ortuno D, Rose PE, Schenkel LB, Taborn K, Wang J, Wang Y, Yu V, Weiss MM..  (2016)  Application of a Parallel Synthetic Strategy in the Discovery of Biaryl Acyl Sulfonamides as Efficient and Selective NaV1.7 Inhibitors.,  59  (17): [PMID:27441383] [10.1021/acs.jmedchem.6b00425]

Source

Source(1):

• Scientific Literature