cis-2-Chloro-5-{4-[1-(4-methylsulfanyl-phenyl)-methylidene]-5-oxo-4,5-dihydro-imidazol-1-ylsulfamoyl}-benzoic acid

ID: ALA213158

PubChem CID: 44415219

Max Phase: Preclinical

Molecular Formula: C18H14ClN3O5S2

Molecular Weight: 451.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccc(/C=C2\N=CN(NS(=O)(=O)c3ccc(Cl)c(C(=O)O)c3)C2=O)cc1

Standard InChI:  InChI=1S/C18H14ClN3O5S2/c1-28-12-4-2-11(3-5-12)8-16-17(23)22(10-20-16)21-29(26,27)13-6-7-15(19)14(9-13)18(24)25/h2-10,21H,1H3,(H,24,25)/b16-8-

Standard InChI Key:  KGOACNOBHXCLBC-PXNMLYILSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.7694  -13.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7682  -14.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831  -14.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1995  -14.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966  -13.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4813  -12.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9096  -12.9020    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917  -12.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6286  -12.4975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3384  -12.9180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4124  -13.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183  -13.9209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6382  -13.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0905  -12.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2688  -11.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594  -13.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9385  -13.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5933  -14.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0716  -15.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8937  -15.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2352  -14.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7549  -13.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3704  -15.8127    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1915  -15.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0521  -12.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0519  -12.0849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377  -13.3226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0534  -14.5601    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  3  4  2  0
 15 16  2  0
  7  8  2  0
 14 17  2  0
 17 18  1  0
  7  9  2  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  7 10  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 18  1  0
 12 13  2  0
  5  6  2  0
 24 25  1  0
 21 24  1  0
  6  1  1  0
  1  2  2  0
  5  7  1  0
 26 27  1  0
 26 28  2  0
  1 26  1  0
 11 12  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA213158

   2-chloro-5-[[(4Z)-4-[(4-methylsulfanylphenyl)methylidene]-5-oxoimidazol-1-yl]sulfamoyl]benzoic acid

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: 451.91

Molecular Weight (Monoisotopic): 451.0063

AlogP: 2.87

#Rotatable Bonds: 6

Polar Surface Area: 116.14

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.73

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: -0.80

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.27

References

1. Schepetkin IA, Khlebnikov AI, Kirpotina LN, Quinn MT..  (2006)  Novel small-molecule inhibitors of anthrax lethal factor identified by high-throughput screening.,  49  (17): [PMID:16913712] [10.1021/jm0605132]

Source

Source(1):

• Scientific Literature