N-(4-(aminomethyl)phenyl)-4-(3-hexylureido)benzenesulfonamide

ID: ALA1078533

PubChem CID: 46882807

Max Phase: Preclinical

Molecular Formula: C20H28N4O3S

Molecular Weight: 404.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H28N4O3S/c1-2-3-4-5-14-22-20(25)23-17-10-12-19(13-11-17)28(26,27)24-18-8-6-16(15-21)7-9-18/h6-13,24H,2-5,14-15,21H2,1H3,(H2,22,23,25)

Standard InChI Key:  AGUXGNJNKDLAHB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   19.0430    1.6808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4601    0.9634    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.8728    1.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8936   -0.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6068   -0.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3200   -0.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0331   -0.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7463   -0.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4595   -0.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1752   -0.6957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8898   -0.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6054   -0.6940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8888    0.5439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3201   -0.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0349   -0.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7491   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7486    0.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0279    0.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3166    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1788    0.5489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8938    0.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6081    0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3225    0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3226    1.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6023    2.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8907    1.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0370    2.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7529    1.7900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  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
 12 14  1  0
 24 27  1  0
  7  8  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078533

   N-(4-(aminomethyl)phenyl)-4-(3-hexylureido)benzenesulfonamide

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: 404.54

Molecular Weight (Monoisotopic): 404.1882

AlogP: 3.65

#Rotatable Bonds: 10

Polar Surface Area: 113.32

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.98

CX Basic pKa: 9.28

CX LogP: 2.08

CX LogD: 1.49

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -1.37

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