2-Isopropyl-5-methylcyclohexyl 4-(3-(2,6-Difluorobenzoyl)ureido)benzenesulfonate

ID: ALA2289192

PubChem CID: 71540994

Max Phase: Preclinical

Molecular Formula: C24H28F2N2O5S

Molecular Weight: 494.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CCC(C(C)C)C(OS(=O)(=O)c2ccc(NC(=O)NC(=O)c3c(F)cccc3F)cc2)C1

Standard InChI:  InChI=1S/C24H28F2N2O5S/c1-14(2)18-12-7-15(3)13-21(18)33-34(31,32)17-10-8-16(9-11-17)27-24(30)28-23(29)22-19(25)5-4-6-20(22)26/h4-6,8-11,14-15,18,21H,7,12-13H2,1-3H3,(H2,27,28,29,30)

Standard InChI Key:  DJHSDHOZIMKDFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   18.0525  -13.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0566  -13.9542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.7623  -13.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1187  -13.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9341  -13.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3410  -12.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9336  -11.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1151  -11.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7119  -12.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3411  -11.1238    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3421  -13.9508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.1582  -12.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5666  -13.2462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5670  -11.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3838  -13.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7923  -13.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7926  -12.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6094  -13.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0156  -14.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8321  -14.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2417  -13.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8288  -13.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0138  -13.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4682  -14.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2854  -14.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6894  -15.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5030  -15.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9147  -14.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5065  -13.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6867  -13.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2784  -16.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4613  -16.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6847  -16.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9168  -13.2496    0.0000 C   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
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 15 16  1  0
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 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
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 26 31  1  0
 31 32  1  0
 31 33  1  0
 29 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289192

   (5-Methyl-2-propan-2-ylcyclohexyl) 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: 494.56

Molecular Weight (Monoisotopic): 494.1687

AlogP: 5.09

#Rotatable Bonds: 6

Polar Surface Area: 101.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.04

CX Basic pKa: ┄

CX LogP: 5.75

CX LogD: 5.74

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.54

Np Likeness Score: -0.78

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