4-((bromodichloromethyl)sulfonyl)-N-cyclopentyl-2-nitroaniline

ID: ALA5186592

PubChem CID: 15992207

Max Phase: Preclinical

Molecular Formula: C12H13BrCl2N2O4S

Molecular Weight: 432.12

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(S(=O)(=O)C(Cl)(Cl)Br)ccc1NC1CCCC1

Standard InChI:  InChI=1S/C12H13BrCl2N2O4S/c13-12(14,15)22(20,21)9-5-6-10(11(7-9)17(18)19)16-8-3-1-2-4-8/h5-8,16H,1-4H2

Standard InChI Key:  AOTFCXHSBXYTQC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    0.9958    1.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    1.3889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330    1.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    0.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    0.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933   -0.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078   -1.0857    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -1.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945   -1.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4223   -0.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4223    0.1517    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1367   -1.0857    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1367   -0.2606    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.2832   -1.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331   -0.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331    0.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1477    0.5641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621    0.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6661   -0.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1367   -0.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448    0.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  2  4  1  0
  5  4  1  0
  6  5  2  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 14  6  1  0
 15 14  2  0
 16 15  1  0
  4 16  2  0
 17 16  1  0
 18 17  1  0
 19 18  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  0
 18 22  1  0
M  CHG  2   1  -1   2   1
M  END

Alternative Forms

1. Parent:

   

   ALA5186592

   4-[bromo(dichloro)methyl]sulfonyl-N-cyclopentyl-2-nitroaniline

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: 432.12

Molecular Weight (Monoisotopic): 429.9156

AlogP: 4.21

#Rotatable Bonds: 5

Polar Surface Area: 89.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.30

CX Basic pKa: ┄

CX LogP: 5.11

CX LogD: 5.11

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.43

Np Likeness Score: -1.34

References

1. Rodriguez M, Kannangara A, Chlebowicz J, Akella R, He H, Tambar UK, Goldsmith EJ..  (2022)  Synthesis and Structural Characterization of Novel Trihalo-sulfone Inhibitors of WNK1.,  13  (10.0): [PMID:36262391] [10.1021/acsmedchemlett.2c00216]

Source

Source(1):

• Scientific Literature