5-[2-(5-chloro-2-methoxybenzamido)ethyl]-2,4-dimethoxy-benzenesulfonyl-3-methlthiourea

ID: ALA11827

PubChem CID: 10767760

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)c(OC)cc1OC

Standard InChI:  InChI=1S/C20H24ClN3O6S2/c1-22-20(31)24-32(26,27)18-9-12(16(29-3)11-17(18)30-4)7-8-23-19(25)14-10-13(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:  YUXCZTNZTZVAPH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
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   -0.4333   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -2.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0500   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9458   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5333   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9625   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -2.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6375   -2.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5708   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -1.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0958   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -4.1542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5708   -1.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0958   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  8  1  0
  5  3  2  0
  6  2  2  0
  7  2  1  0
  8 18  1  0
  9  6  1  0
 10  1  2  0
 11  1  2  0
 12 13  1  0
 13  7  2  0
 14  4  2  0
 15  4  1  0
 16  5  1  0
 17  8  2  0
 18 27  1  0
 19  5  1  0
 20 14  1  0
 21 15  2  0
 22  6  1  0
 23 12  1  0
 24 21  1  0
 25 21  1  0
 26 14  1  0
 27 28  1  0
 28 13  1  0
 29 19  1  0
 30 22  1  0
 31 23  1  0
 32 26  1  0
 12  9  2  0
 24 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA11827

   5-chloro-N-[2-[2,4-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: 6.35

CX Basic pKa: 1.36

CX LogP: 2.67

CX LogD: 1.84

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.27

Np Likeness Score: -1.15

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