N,N'-(1,2-Phenylene)bis(4-methoxybenzothioamide)

ID: ALA1641769

PubChem CID: 53319208

Max Phase: Preclinical

Molecular Formula: C23H22N2O2S2

Molecular Weight: 422.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=S)Nc2ccccc2N(C)C(=S)c2ccc(OC)cc2)cc1

Standard InChI:  InChI=1S/C23H22N2O2S2/c1-25(23(29)17-10-14-19(27-3)15-11-17)21-7-5-4-6-20(21)24-22(28)16-8-12-18(26-2)13-9-16/h4-15H,1-3H3,(H,24,28)

Standard InChI Key:  DECUUEACHQQGQS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.7563  -11.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4693  -11.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886  -11.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855  -10.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673  -10.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035  -11.8905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042  -12.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6190  -13.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1901  -13.1287    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171  -13.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3311  -14.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0463  -13.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0428  -13.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282  -12.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8978  -10.2315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8938   -9.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6062   -8.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1772   -8.9976    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3198   -9.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0317   -8.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0281   -8.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -7.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5976   -8.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144  -10.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7400   -7.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4570   -8.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7616  -14.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7635  -15.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
 14 15  2  0
 15  9  1  0
  3  4  2  0
  5 16  1  0
  7  8  1  0
 16 17  1  0
 17 18  1  0
  8  9  1  0
 17 19  2  0
  4  5  1  0
 18 20  2  0
  8 10  2  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
  9 11  2  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 18  1  0
 11 12  1  0
 16 25  1  0
  6  1  1  0
 22 26  1  0
 12 13  2  0
 26 27  1  0
  1  2  2  0
 13 28  1  0
 13 14  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1641769

   4-methoxy-N-[2-[(4-methoxybenzenecarbothioyl)-methylamino]phenyl]benzenecarbothioamide

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: 422.58

Molecular Weight (Monoisotopic): 422.1123

AlogP: 5.30

#Rotatable Bonds: 6

Polar Surface Area: 33.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.87

CX Basic pKa: ┄

CX LogP: 5.49

CX LogD: 5.49

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -0.73

References

1. Brunhofer G, Granig WH, Studenik CR, Erker T..  (2011)  A journey from benzanilides to dithiobenzanilides: Synthesis of selective spasmolytic compounds.,  19  (2): [PMID:21185194] [10.1016/j.bmc.2010.11.043]

Source

Source(1):

• Scientific Literature