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

ID: ALA3360587

PubChem CID: 101879106

Max Phase: Preclinical

Molecular Formula: C19H24N4O4S

Molecular Weight: 404.49

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  WTYBGEXCVVUKCD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   14.0945  -12.1093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5072  -11.4035    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.6896  -11.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0657   -6.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3555   -6.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6420   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9319   -6.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0624   -5.6628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7792   -6.8898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7825   -7.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4960   -8.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4994   -8.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2129   -9.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2162  -10.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5060  -10.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7925  -10.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7892   -9.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2225   -6.4957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5123   -6.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7989   -6.5015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5157   -7.7285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8055   -8.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8089   -8.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0987   -9.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3852   -8.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3819   -8.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0920   -7.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2187  -11.8119    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  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 15  2  1  0
  9 10  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 21 22  1  0
  7 18  1  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3360587

   4-(phenylcarbamoylamino)-N-[2-(4-sulfamoylphenyl)ethyl]butanamide

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: 1.59

#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: 1.14

CX LogD: 1.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.54

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