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

ID: ALA12475

PubChem CID: 10815292

Max Phase: Preclinical

Molecular Formula: C20H24ClN3O6S2

Molecular Weight: 502.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN/C(S)=N/S(=O)(=O)c1cc(CCNC(=O)c2cc(Cl)ccc2OC)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H24ClN3O6S2/c1-22-20(31)24-32(26,27)17-10-12(9-16(29-3)18(17)30-4)7-8-23-19(25)14-11-13(21)5-6-15(14)28-2/h5-6,9-11H,7-8H2,1-4H3,(H,23,25)(H2,22,24,31)

Standard InChI Key:  LAZPSKFAVHYPBG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    0.3375   -1.5750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -1.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8000   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7125   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -1.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -1.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8000   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -2.1750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833   -0.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -1.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -1.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8458   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -0.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    0.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8458   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333   -3.1042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208   -0.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3250    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8458   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  7  1  0
  5  2  2  0
  6  3  2  0
  7 18  1  0
  8  5  1  0
  9  1  2  0
 10  1  2  0
 11  2  1  0
 12  4  2  0
 13  4  1  0
 14  6  1  0
 15 17  1  0
 16  7  2  0
 17 11  2  0
 18 27  1  0
 19  6  1  0
 20 12  1  0
 21  5  1  0
 22 13  2  0
 23  8  1  0
 24 22  1  0
 25 22  1  0
 26 12  1  0
 27 28  1  0
 28 17  1  0
 29 19  1  0
 30 21  1  0
 31 23  1  0
 32 26  1  0
 15  8  2  0
 24 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA12475

   5-chloro-N-[2-[3,4-dimethoxy-5-(methylcarbamothioylsulfamoyl)phenyl]ethyl]-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: 502.01

Molecular Weight (Monoisotopic): 501.0795

AlogP: 2.53

#Rotatable Bonds: 9

Polar Surface Area: 115.32

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.36

CX Basic pKa: 1.35

CX LogP: 2.67

CX LogD: 1.84

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.27

Np Likeness Score: -0.99

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