6-chloro-3-(3,4-dichlorophenoxy)-2-(3-(3-(trifluoromethyl)phenyl)ureido)benzenesulfonic acid

ID: ALA576555

PubChem CID: 423228

Max Phase: Preclinical

Molecular Formula: C20H12Cl3F3N2O5S

Molecular Weight: 555.75

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-152166 | CHEMBL576555|NSC-152166|BDBM50300688|6-chloro-3-(3,4-dichlorophenoxy)-2-(3-(3-(trifluoromethyl)phenyl)ureido)benzenesulfonic acid

Canonical SMILES:  O=C(Nc1cccc(C(F)(F)F)c1)Nc1c(Oc2ccc(Cl)c(Cl)c2)ccc(Cl)c1S(=O)(=O)O

Standard InChI:  InChI=1S/C20H12Cl3F3N2O5S/c21-13-5-4-12(9-15(13)23)33-16-7-6-14(22)18(34(30,31)32)17(16)28-19(29)27-11-3-1-2-10(8-11)20(24,25)26/h1-9H,(H2,27,28,29)(H,30,31,32)

Standard InChI Key:  QRHIXNFPZKMURE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.0486   -7.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474   -8.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -8.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -8.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758   -7.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -7.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7620   -9.4819    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -9.8942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4764   -9.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9652   -9.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1938   -8.6549    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -7.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3338   -6.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -5.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508   -4.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357   -4.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -4.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6223   -5.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344   -3.7066    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3326   -8.6559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6185   -8.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -8.6548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191   -7.4179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105   -8.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050   -7.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5183   -7.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341   -7.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321   -8.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182   -8.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0971   -4.5389    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9454   -8.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6610   -8.2479    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9432   -9.4835    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1611   -7.8622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 14 15  1  0
  3  4  2  0
 17 30  1  0
 15 16  2  0
 28 31  1  0
  7  8  1  0
 31 32  1  0
 16 17  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA576555

   6-Chloro-3-(3,4-dichlorophenoxy)-2-(3-(3-(trifluoromethyl)phenyl)ureido)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: 555.75

Molecular Weight (Monoisotopic): 553.9485

AlogP: 7.35

#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: -2.78

CX Basic pKa: ┄

CX LogP: 4.88

CX LogD: 4.76

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.29

Np Likeness Score: -1.36

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