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

ID: ALA3360588

PubChem CID: 118724329

Max Phase: Preclinical

Molecular Formula: C19H24N4O4S

Molecular Weight: 404.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(CNC(=O)CCCNC(=O)NCc2ccccc2)cc1

Standard InChI:  InChI=1S/C19H24N4O4S/c20-28(26,27)17-10-8-16(9-11-17)13-22-18(24)7-4-12-21-19(25)23-14-15-5-2-1-3-6-15/h1-3,5-6,8-11H,4,7,12-14H2,(H,22,24)(H2,20,26,27)(H2,21,23,25)

Standard InChI Key:  JCCDIFAGFKPVRO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    8.8928  -18.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6005  -17.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3082  -18.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0159  -17.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8928  -18.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1851  -17.7140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1851  -16.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4774  -16.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7697  -16.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620  -16.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620  -15.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7697  -15.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4774  -15.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7236  -18.1226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4313  -17.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1390  -18.1226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4313  -16.8968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1390  -16.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8468  -16.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5545  -16.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2622  -16.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2622  -17.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5545  -18.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8468  -17.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9797  -14.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664  -15.2453    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7968  -14.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6467  -15.6392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  2  0
  1  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
  6  7  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 17 18  1  0
  4 14  1  0
 26 25  2  0
 27 26  2  0
 11 26  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3360588

   ---

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: 404.49

Molecular Weight (Monoisotopic): 404.1518

AlogP: 1.23

#Rotatable Bonds: 9

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: 0.56

CX LogD: 0.56

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.37

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