4-(3-hexylureido)-N-phenylbenzenesulfonamide

ID: ALA1077716

PubChem CID: 46882764

Max Phase: Preclinical

Molecular Formula: C19H25N3O3S

Molecular Weight: 375.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCNC(=O)Nc1ccc(S(=O)(=O)Nc2ccccc2)cc1

Standard InChI:  InChI=1S/C19H25N3O3S/c1-2-3-4-8-15-20-19(23)21-16-11-13-18(14-12-16)26(24,25)22-17-9-6-5-7-10-17/h5-7,9-14,22H,2-4,8,15H2,1H3,(H2,20,21,23)

Standard InChI Key:  ADKICSRVDIFTQJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    4.0250   -6.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4422   -7.3410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8549   -6.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1251   -9.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4119   -8.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6986   -9.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -8.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721   -9.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589   -8.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1568   -9.0003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715   -8.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -8.9986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705   -7.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -8.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168   -8.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7310   -8.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7305   -7.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -7.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2985   -7.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609   -7.7556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8760   -7.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5904   -7.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3049   -7.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3050   -6.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5845   -6.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730   -6.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
  7  8  1  0
 14 15  2  0
  4  5  1  0
 15 16  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA1077716

   4-(3-hexylureido)-N-phenylbenzenesulfonamide

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: 375.49

Molecular Weight (Monoisotopic): 375.1617

AlogP: 4.19

#Rotatable Bonds: 9

Polar Surface Area: 87.30

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.93

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.70

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.57

Np Likeness Score: -1.59

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