N-(2-(3-(4-(aminomethyl)phenyl)propylamino)ethyl)benzo[b]thiophene-5-sulfonamide

ID: ALA379328

PubChem CID: 10294609

Max Phase: Preclinical

Molecular Formula: C20H25N3O2S2

Molecular Weight: 403.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCc1ccc(CCCNCCNS(=O)(=O)c2ccc3sccc3c2)cc1

Standard InChI:  InChI=1S/C20H25N3O2S2/c21-15-17-5-3-16(4-6-17)2-1-10-22-11-12-23-27(24,25)19-7-8-20-18(14-19)9-13-26-20/h3-9,13-14,22-23H,1-2,10-12,15,21H2

Standard InChI Key:  GJNNFTSDQAHBMY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    7.1077  -23.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4172  -23.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4588  -24.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8438  -23.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8855  -24.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1949  -24.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4073  -25.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2301  -25.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5237  -24.7808    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812  -23.1423    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2690  -23.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0933  -22.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435  -24.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0287  -23.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0287  -23.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435  -22.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582  -23.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582  -23.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729  -24.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837  -23.9666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6859  -22.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3967  -23.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1115  -22.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262  -23.1423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5409  -22.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2556  -23.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9664  -22.7301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  2 10  1  0
 10 11  2  0
 10 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA379328

   N-(2-(3-(4-(aminomethyl)phenyl)propylamino)ethyl)benzo[b]thiophene-5-sulfonamide

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: 403.57

Molecular Weight (Monoisotopic): 403.1388

AlogP: 2.86

#Rotatable Bonds: 10

Polar Surface Area: 84.22

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.18

CX Basic pKa: 9.41

CX LogP: 2.56

CX LogD: -0.55

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -1.44

References

1. Miyazaki Y, Kato Y, Manabe T, Shimada H, Mizuno M, Egusa T, Ohkouchi M, Shiromizu I, Matsusue T, Yamamoto I..  (2006)  Synthesis and evaluation of 4-substituted benzylamine derivatives as beta-tryptase inhibitors.,  16  (11): [PMID:16540315] [10.1016/j.bmcl.2006.02.064]

Source

Source(1):

• Scientific Literature