4-(3-phenylureido)-N-(4-sulfamoylbenzyl)-butanamide

ID: ALA3360586

PubChem CID: 118724328

Max Phase: Preclinical

Molecular Formula: C18H22N4O4S

Molecular Weight: 390.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(CNC(=O)CCCNC(=O)Nc2ccccc2)cc1

Standard InChI:  InChI=1S/C18H22N4O4S/c19-27(25,26)16-10-8-14(9-11-16)13-21-17(23)7-4-12-20-18(24)22-15-5-2-1-3-6-15/h1-3,5-6,8-11H,4,7,12-13H2,(H,21,23)(H2,19,25,26)(H2,20,22,24)

Standard InChI Key:  RAJOFUINILIQDK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   15.1015   -8.1265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6971   -8.8364    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5141   -8.8317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1480   -5.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4362   -6.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7244   -5.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125   -6.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1480   -5.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8558   -6.3787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8558   -7.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5676   -7.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2794   -7.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9913   -7.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9913   -8.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2794   -8.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5676   -8.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3007   -5.9660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889   -6.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770   -5.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889   -7.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770   -7.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770   -8.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652   -8.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575   -8.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575   -7.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652   -7.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7001   -9.6551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  2  0
  4  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
  9 10  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 21  1  0
  7 17  1  0
 14  2  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3360586

   ---

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: 390.47

Molecular Weight (Monoisotopic): 390.1362

AlogP: 1.55

#Rotatable Bonds: 8

Polar Surface Area: 130.39

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.22

CX Basic pKa: ┄

CX LogP: 0.85

CX LogD: 0.85

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.75

References

1. Ceruso M, Antel S, Vullo D, Scozzafava A, Supuran CT..  (2014)  Inhibition studies of new ureido-substituted sulfonamides incorporating a GABA moiety against human carbonic anhydrase isoforms I-XIV.,  22  (24): [PMID:25468040] [10.1016/j.bmc.2014.10.041]

Source

Source(1):

• Scientific Literature