6-chloro-2-(3-(4-chloro-2-methylphenyl)ureido)-3-(4-chlorophenoxy)benzenesulfonic acid

ID: ALA575313

PubChem CID: 423151

Max Phase: Preclinical

Molecular Formula: C20H15Cl3N2O5S

Molecular Weight: 501.78

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-151179 | CHEMBL575313|NSC-151179|BDBM50300689|6-chloro-2-(3-(4-chloro-2-methylphenyl)ureido)-3-(4-chlorophenoxy)benzenesulfonic acid

Canonical SMILES:  Cc1cc(Cl)ccc1NC(=O)Nc1c(Oc2ccc(Cl)cc2)ccc(Cl)c1S(=O)(=O)O

Standard InChI:  InChI=1S/C20H15Cl3N2O5S/c1-11-10-13(22)4-8-16(11)24-20(26)25-18-17(30-14-5-2-12(21)3-6-14)9-7-15(23)19(18)31(27,28)29/h2-10H,1H3,(H2,24,25,26)(H,27,28,29)

Standard InChI Key:  DRXBXQAFEIOKPV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   12.1027   -1.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1016   -2.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8164   -2.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5328   -2.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5300   -1.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8146   -0.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8162   -3.3235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1016   -3.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5306   -3.7362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0194   -3.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2480   -2.4966    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3882   -0.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3880   -0.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1048    0.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1049    1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3898    1.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6731    1.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6765    0.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3885    2.4518    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3868   -2.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6726   -2.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9578   -2.4965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6733   -1.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2437   -2.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2492   -1.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -0.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8201   -1.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8221   -2.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360   -2.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1054   -0.8443    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5385   -3.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 15 16  2  0
  7  8  1  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  7  9  2  0
 16 19  1  0
  4  5  1  0
  2 20  1  0
  7 10  2  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
  4 11  1  0
 21 23  2  0
  5  6  2  0
 22 24  1  0
  1 12  1  0
 24 25  2  0
  6  1  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
  1  2  2  0
 27 28  1  0
 13 14  2  0
 28 29  2  0
 29 24  1  0
  3  7  1  0
 27 30  1  0
 14 15  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA575313

   6-Chloro-2-(3-(4-chloro-2-methylphenyl)ureido)-3-(4-chlorophenoxy)benzenesulfonic 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: 501.78

Molecular Weight (Monoisotopic): 499.9767

AlogP: 6.64

#Rotatable Bonds: 5

Polar Surface Area: 104.73

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -2.53

CX Basic pKa: ┄

CX LogP: 4.61

CX LogD: 4.40

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: -1.32

References

1. Miguet L, Zervosen A, Gerards T, Pasha FA, Luxen A, Distèche-Nguyen M, Thomas A..  (2009)  Discovery of new inhibitors of resistant Streptococcus pneumoniae penicillin binding protein (PBP) 2x by structure-based virtual screening.,  52  (19): [PMID:19746934] [10.1021/jm900625q]

Source

Source(1):

• Scientific Literature