(E)-N-(4-(N-(3-methoxypyrazin-2-yl)sulfamoyl)phenyl)-3-(5-nitrothiophen-2-yl)acrylamide

ID: ALA3220918

Cas Number: 432531-71-0

PubChem CID: 1566236

Product Number: N276059, Order Now?

Max Phase: Preclinical

Molecular Formula: C18H15N5O6S2

Molecular Weight: 461.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nccnc1NS(=O)(=O)c1ccc(NC(=O)/C=C/c2ccc([N+](=O)[O-])s2)cc1

Standard InChI:  InChI=1S/C18H15N5O6S2/c1-29-18-17(19-10-11-20-18)22-31(27,28)14-6-2-12(3-7-14)21-15(24)8-4-13-5-9-16(30-13)23(25)26/h2-11H,1H3,(H,19,22)(H,21,24)/b8-4+

Standard InChI Key:  FNPPHVLYVGMZMZ-XBXARRHUSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   16.5175   -3.6910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.1077   -4.4071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9327   -4.4040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6613   -3.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6601   -4.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3750   -4.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0914   -4.5269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0886   -3.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3732   -3.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8015   -3.2812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2305   -3.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9448   -3.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6573   -3.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6547   -2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9336   -2.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2241   -2.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3670   -2.0325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0836   -2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7960   -2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0878   -3.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5126   -2.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2246   -2.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8982   -2.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5539   -1.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2803   -1.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4556   -1.2285    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.7447   -0.5299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3918    0.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5721   -0.5954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3706   -2.4622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0839   -2.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10  1  1  0
  1 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
 27 28  2  0
 27 29  1  0
 25 27  1  0
  9 30  1  0
 30 31  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3220918

   Necrosulfonamide

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: 461.48

Molecular Weight (Monoisotopic): 461.0464

AlogP: 2.91

#Rotatable Bonds: 8

Polar Surface Area: 153.42

Molecular Species: ACID

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.70

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 1.79

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -2.09

References

1. Liao D, Sun L, Liu W, He S, Wang X, Lei X.  (2014)  Necrosulfonamide inhibits necroptosis by selectively targeting the mixed lineage kinase domain-like protein,  5  (3): [10.1039/C3MD00278K]

2. Zhuang C, Chen F..  (2020)  Small-Molecule Inhibitors of Necroptosis: Current Status and Perspectives.,  63  (4): [PMID:31622096] [10.1021/acs.jmedchem.9b01317]

Source

Source(1):

• Scientific Literature