4-Chlorobutyl 4-(3-(2,6-Difluorobenzoyl)ureido)-benzenesulfonate

ID: ALA2288959

PubChem CID: 71541203

Max Phase: Preclinical

Molecular Formula: C18H17ClF2N2O5S

Molecular Weight: 446.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC(=O)c1c(F)cccc1F)Nc1ccc(S(=O)(=O)OCCCCCl)cc1

Standard InChI:  InChI=1S/C18H17ClF2N2O5S/c19-10-1-2-11-28-29(26,27)13-8-6-12(7-9-13)22-18(25)23-17(24)16-14(20)4-3-5-15(16)21/h3-9H,1-2,10-11H2,(H2,22,23,24,25)

Standard InChI Key:  HQRCBYSUTZEZQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   28.0610  -19.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0652  -19.9717    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.7708  -19.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1272  -19.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9426  -19.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3496  -18.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9422  -17.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1236  -17.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7204  -18.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3497  -17.1413    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.3507  -19.9682    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.1667  -18.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5752  -19.2637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5755  -17.8483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3924  -19.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8008  -19.9717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8011  -18.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6180  -19.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0242  -20.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8406  -20.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2502  -19.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8374  -19.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0223  -19.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4767  -20.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2939  -20.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6979  -21.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5151  -21.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9199  -22.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7371  -22.1068    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  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
  7 10  1  0
  5 11  1  0
  6 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21  2  1  0
  2 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288959

   4-Chlorobutyl 4-[(2,6-difluorobenzoyl)carbamoylamino]benzenesulfonate

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: 446.86

Molecular Weight (Monoisotopic): 446.0515

AlogP: 3.65

#Rotatable Bonds: 8

Polar Surface Area: 101.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.04

CX Basic pKa: ┄

CX LogP: 3.81

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.37

Np Likeness Score: -1.40

References

1. Sun R, Wang Z, Li Y, Xiong L, Liu Y, Wang Q..  (2013)  Design, synthesis, and insecticidal evaluation of new benzoylureas containing amide and sulfonate groups based on the sulfonylurea receptor protein binding site for diflubenzuron and glibenclamide.,  61  (3): [PMID:23305601] [10.1021/jf304468b]

Source

Source(1):

• Scientific Literature