Methyl 5-(N-(3-(3,4-Dichlorobenzylthio)thiophene-2-carbonyl)-sulfamoyl)-2-methoxybenzoate

ID: ALA1910962

PubChem CID: 54757904

Max Phase: Preclinical

Molecular Formula: C21H17Cl2NO6S3

Molecular Weight: 546.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(S(=O)(=O)NC(=O)c2sccc2SCc2ccc(Cl)c(Cl)c2)ccc1OC

Standard InChI:  InChI=1S/C21H17Cl2NO6S3/c1-29-17-6-4-13(10-14(17)21(26)30-2)33(27,28)24-20(25)19-18(7-8-31-19)32-11-12-3-5-15(22)16(23)9-12/h3-10H,11H2,1-2H3,(H,24,25)

Standard InChI Key:  IPLQJJXGYWHQSP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   18.8614  -22.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4531  -23.1653    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.2778  -23.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6265  -23.2694    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3037  -22.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0550  -21.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2260  -21.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9618  -22.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0243  -23.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0366  -24.0157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7324  -22.7678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5463  -21.3352    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.3711  -21.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7897  -20.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6123  -20.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0307  -19.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6244  -19.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7951  -19.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3803  -19.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0419  -18.5001    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.8556  -19.9379    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.4653  -23.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7506  -24.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7622  -25.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4866  -25.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2006  -25.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1854  -24.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4997  -26.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7918  -26.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9224  -25.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9373  -26.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6292  -25.1942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3510  -25.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  2  1  2  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1910962

   Methyl 5-[[3-[(3,4-dichlorophenyl)methylsulfanyl]thiophene-2-carbonyl]sulfamoyl]-2-methoxybenzoate

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: 546.48

Molecular Weight (Monoisotopic): 544.9595

AlogP: 5.26

#Rotatable Bonds: 8

Polar Surface Area: 98.77

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.02

CX Basic pKa: ┄

CX LogP: 5.64

CX LogD: 4.70

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.30

Np Likeness Score: -1.70

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