5-(4-Dodecylphenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide

ID: ALA1685058

PubChem CID: 53326304

Max Phase: Preclinical

Molecular Formula: C20H32N4O4S3

Molecular Weight: 488.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCc1ccc(S(=O)(=O)Nc2nnc(S(N)(=O)=O)s2)cc1

Standard InChI:  InChI=1S/C20H32N4O4S3/c1-2-3-4-5-6-7-8-9-10-11-12-17-13-15-18(16-14-17)31(27,28)24-19-22-23-20(29-19)30(21,25)26/h13-16H,2-12H2,1H3,(H,22,24)(H2,21,25,26)

Standard InChI Key:  FLHFDHASGBHRBU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    9.0759  -13.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0776  -12.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794  -12.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815  -10.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988    1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    0.9001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    2.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5998    3.0012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995    3.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404    5.2322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5083    5.5410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2556    4.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2496    3.1278    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7453    4.0808    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4533    5.0497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2308    2.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9384    3.9523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  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
 16 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  1  0
 26 28  1  0
 28 29  2  0
 28 30  2  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1685058

   5-(4-Dodecylphenylsulfonamido)-1,3,4-thiadiazole-2-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: 488.70

Molecular Weight (Monoisotopic): 488.1586

AlogP: 4.45

#Rotatable Bonds: 15

Polar Surface Area: 132.11

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.42

CX Basic pKa: ┄

CX LogP: 5.61

CX LogD: 4.51

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -1.14

References

1. Ahad AM, Zuohe S, Du-Cuny L, Moses SA, Zhou LL, Zhang S, Powis G, Meuillet EJ, Mash EA..  (2011)  Development of sulfonamide AKT PH domain inhibitors.,  19  (6): [PMID:21353784] [10.1016/j.bmc.2011.01.049]

2.  (2016)  Small molecule inhibitors of the pleckstrin homology domain and methods for using same, 

3.  (2017)  Inhibitors of grb2-associated binding protein 1 (gab1) and methods of treating cancer using the same, 

Source

Source(3):

• Scientific Literature
• BindingDB Database
• Patent Bioactivity Data