N-(4-(2-aminoethyl)phenyl)-4-(3-hexylureido)benzenesulfonamide

ID: ALA1077839

PubChem CID: 46882766

Max Phase: Preclinical

Molecular Formula: C21H30N4O3S

Molecular Weight: 418.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H30N4O3S/c1-2-3-4-5-16-23-21(26)24-18-10-12-20(13-11-18)29(27,28)25-19-8-6-17(7-9-19)14-15-22/h6-13,25H,2-5,14-16,22H2,1H3,(H2,23,24,26)

Standard InChI Key:  HCGBUHQBTSGJRX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    3.8117  -13.2786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2288  -13.9959    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6415  -13.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3372  -15.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241  -15.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109  -15.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978  -15.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846  -15.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7715  -15.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0560  -15.6549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6587  -15.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743  -15.6532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6577  -14.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0889  -15.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036  -15.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5178  -15.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173  -14.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966  -14.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855  -14.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474  -14.4103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6624  -13.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3767  -14.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0911  -13.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0912  -13.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708  -12.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6594  -13.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8055  -12.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5213  -13.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2357  -12.7552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  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
 14 15  2  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077839

   N-(4-(2-aminoethyl)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: 418.56

Molecular Weight (Monoisotopic): 418.2039

AlogP: 3.69

#Rotatable Bonds: 11

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: 8.05

CX Basic pKa: 9.80

CX LogP: 2.33

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: -1.23

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