5-(N-(3-(3,4-Dichlorobenzylthio)thiophene-2-carbonyl)sulfamoyl)-2-methoxybenzoic acid

ID: ALA1910889

Cas Number: 1336982-56-9

PubChem CID: 54751678

Max Phase: Preclinical

Molecular Formula: C20H15Cl2NO6S3

Molecular Weight: 532.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)NC(=O)c2sccc2SCc2ccc(Cl)c(Cl)c2)cc1C(=O)O

Standard InChI:  InChI=1S/C20H15Cl2NO6S3/c1-29-16-5-3-12(9-13(16)20(25)26)32(27,28)23-19(24)18-17(6-7-30-18)31-10-11-2-4-14(21)15(22)8-11/h2-9H,10H2,1H3,(H,23,24)(H,25,26)

Standard InChI Key:  HBYORZQNJPQOQI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.9102  -22.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5019  -23.5704    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3266  -23.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6757  -23.6744    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3529  -23.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042  -22.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2753  -22.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0111  -23.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0733  -23.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0856  -24.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7814  -23.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5954  -21.7406    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4202  -21.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8387  -21.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6611  -21.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0795  -20.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6732  -19.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8441  -19.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4294  -20.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0907  -18.9058    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9043  -20.3434    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.5141  -24.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7996  -24.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8112  -25.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5354  -26.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2494  -25.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2342  -24.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5485  -26.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8408  -27.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9711  -26.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9859  -26.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6778  -25.5990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
 16 17  2  0
  5  9  1  0
 17 18  1  0
  3  2  2  0
 18 19  2  0
 19 14  1  0
  9 10  2  0
 17 20  1  0
  5  6  2  0
 16 21  1  0
 11  2  1  0
  9 11  1  0
  2 22  1  0
 22 23  2  0
  6 12  1  0
 23 24  1  0
  4  5  1  0
 24 25  2  0
 12 13  1  0
 25 26  1  0
  6  7  1  0
 26 27  2  0
 27 22  1  0
 13 14  1  0
 25 28  1  0
  7  8  2  0
 28 29  1  0
 14 15  2  0
 26 30  1  0
  8  4  1  0
 30 31  2  0
 15 16  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1910889

   5-[({3-[(3,4-Dichlorobenzyl)sulfanyl]thiophen-2-Yl}carbonyl)sulfamoyl]-2-Methoxybenzoic Acid

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: 532.45

Molecular Weight (Monoisotopic): 530.9439

AlogP: 5.17

#Rotatable Bonds: 8

Polar Surface Area: 109.77

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.28

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 0.94

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.67

References

1. Sheriff S, Beno BR, Zhai W, Kostich WA, McDonnell PA, Kish K, Goldfarb V, Gao M, Kiefer SE, Yanchunas J, Huang Y, Shi S, Zhu S, Dzierba C, Bronson J, Macor JE, Appiah KK, Westphal RS, O'Connell J, Gerritz SW..  (2011)  Small molecule receptor protein tyrosine phosphatase γ (RPTPγ) ligands that inhibit phosphatase activity via perturbation of the tryptophan-proline-aspartate (WPD) loop.,  54  (19): [PMID:21882820] [10.1021/jm2003766]

Source

Source(1):

• Scientific Literature