1-(2-Nitro-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester

ID: ALA358207

Cas Number: 142529-00-8

PubChem CID: 464839

Max Phase: Preclinical

Molecular Formula: C13H12N2O6S

Molecular Weight: 324.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cccn1S(=O)(=O)c1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C13H12N2O6S/c1-2-21-13(16)11-7-5-9-14(11)22(19,20)12-8-4-3-6-10(12)15(17)18/h3-9H,2H2,1H3

Standard InChI Key:  VFHJYKJGNBSYMB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    3.3292   -2.8042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -3.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -4.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -1.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -3.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -2.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -1.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -0.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -5.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -3.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  1  0
  7  4  1  0
  8  1  2  0
  9  1  2  0
 10  2  1  0
 11  4  2  0
 12  6  1  0
 13  6  2  0
 14 10  2  0
 15  7  2  0
 16  3  2  0
 17  7  1  0
 18  5  2  0
 19 17  1  0
 20 16  1  0
 21 20  2  0
 22 19  1  0
 11 14  1  0
 21 18  1  0
M  CHG  2   6   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA358207

   1H-Pyrrole-2-carboxylic acid, 1-((2-nitrophenyl)sulfonyl)-, ethyl ester

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: 324.31

Molecular Weight (Monoisotopic): 324.0416

AlogP: 1.81

#Rotatable Bonds: 5

Polar Surface Area: 108.51

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.47

Np Likeness Score: -1.59

References

1. Artico M, Silvestri R, Massa S, Loi AG, Corrias S, Piras G, La Colla P..  (1996)  2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones.,  39  (2): [PMID:8558522] [10.1021/jm950568w]

2. Ahmad S, Alam O, Naim MJ, Shaquiquzzaman M, Alam MM, Iqbal M..  (2018)  Pyrrole: An insight into recent pharmacological advances with structure activity relationship.,  157  [PMID:30119011] [10.1016/j.ejmech.2018.08.002]

Source

Source(1):

• Scientific Literature