4-(3-hexylureido)-N-(4-(2-hydroxy-2-methylpropyl)phenyl)benzenesulfonamide

ID: ALA1077629

PubChem CID: 46882806

Max Phase: Preclinical

Molecular Formula: C23H33N3O4S

Molecular Weight: 447.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCNC(=O)Nc1ccc(S(=O)(=O)Nc2ccc(CC(C)(C)O)cc2)cc1

Standard InChI:  InChI=1S/C23H33N3O4S/c1-4-5-6-7-16-24-22(27)25-19-12-14-21(15-13-19)31(29,30)26-20-10-8-18(9-11-20)17-23(2,3)28/h8-15,26,28H,4-7,16-17H2,1-3H3,(H2,24,25,27)

Standard InChI Key:  VTKKRJPEDJJDSW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    3.5672    1.4627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9839    0.7459    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3963    1.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5756   -0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1504   -0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4378   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7252   -0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0126   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -0.9117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -0.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -0.9100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4156    0.3267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8457   -0.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599   -0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2735   -0.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729    0.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5528    0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8422    0.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7021    0.3318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4164    0.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1302    0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441    0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8441    1.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1243    1.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4134    1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5579    1.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2733    1.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9871    1.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2748    0.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9846    1.1627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
 16 17  2  0
  3  2  2  0
 17 18  1  0
  9 10  1  0
 18 19  2  0
 19 14  1  0
 17  2  1  0
  5  6  1  0
  2 20  1  0
 10 11  1  0
 20 21  1  0
 21 22  2  0
 11 12  1  0
 22 23  1  0
  6  7  1  0
 23 24  2  0
 11 13  2  0
 24 25  1  0
  2  1  2  0
 25 26  2  0
 26 21  1  0
 12 14  1  0
 24 27  1  0
  7  8  1  0
 27 28  1  0
 14 15  2  0
 28 29  1  0
  4  5  1  0
 28 30  1  0
 15 16  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077629

   1-Hexyl-3-[4-[[4-(2-hydroxy-2-methylpropyl)phenyl]sulfamoyl]phenyl]urea

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: 447.60

Molecular Weight (Monoisotopic): 447.2192

AlogP: 4.50

#Rotatable Bonds: 11

Polar Surface Area: 107.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.00

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -1.03

References

1. Pasternak A, Goble SD, deJesus RK, Hreniuk DL, Chung CC, Tota MR, Mazur P, Feighner SD, Howard AD, Mills SG, Yang L..  (2009)  Discovery and optimization of novel 4-[(aminocarbonyl)amino]-N-[4-(2-aminoethyl)phenyl]benzenesulfonamide ghrelin receptor antagonists.,  19  (21): [PMID:19767208] [10.1016/j.bmcl.2009.08.076]

Source

Source(1):

• Scientific Literature