5-[2-(5-chloro-2-methoxybenzamido)ethyl]-2-bromo-benzenesulfonyl-3-methlthiourea

ID: ALA12541

PubChem CID: 10839722

Max Phase: Preclinical

Molecular Formula: C18H19BrClN3O4S2

Molecular Weight: 520.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN/C(S)=N/S(=O)(=O)c1cc(CCNC(=O)c2cc(Cl)ccc2OC)ccc1Br

Standard InChI:  InChI=1S/C18H19BrClN3O4S2/c1-21-18(28)23-29(25,26)16-9-11(3-5-14(16)19)7-8-22-17(24)13-10-12(20)4-6-15(13)27-2/h3-6,9-10H,7-8H2,1-2H3,(H,22,24)(H2,21,23,28)

Standard InChI Key:  ZNEHREIXAZPVNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.5125    0.6208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292    0.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292    0.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    0.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917    1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792    0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5500    0.0250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    0.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625    0.9333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125    1.8208    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -0.9125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458    1.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  1  0
  5  3  2  0
  6 15  1  0
  7  1  2  0
  8  1  2  0
  9  2  2  0
 10  4  2  0
 11  2  1  0
 12  4  1  0
 13  5  1  0
 14  6  2  0
 15 26  1  0
 16  5  1  0
 17  9  1  0
 18 10  1  0
 19 12  2  0
 20 11  2  0
 21  9  1  0
 22 19  1  0
 23 20  1  0
 24 19  1  0
 25 10  1  0
 26 27  1  0
 27 20  1  0
 28 16  1  0
 29 25  1  0
 23 17  2  0
 22 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA12541

   N-[2-[4-bromo-3-(methylcarbamothioylsulfamoyl)phenyl]ethyl]-5-chloro-2-methoxybenzamide

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: 520.86

Molecular Weight (Monoisotopic): 518.9689

AlogP: 3.28

#Rotatable Bonds: 7

Polar Surface Area: 96.86

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.22

CX Basic pKa: 1.38

CX LogP: 3.75

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: -1.33

References

1. Englert HC, Gerlach U, Goegelein H, Hartung J, Heitsch H, Mania D, Scheidler S..  (2001)  Cardioselective K(ATP) channel blockers derived from a new series of m-anisamidoethylbenzenesulfonylthioureas.,  44  (7): [PMID:11297455] [10.1021/jm000985v]

Source

Source(1):

• Scientific Literature