4-((3-aminophenyl)ethynyl)-2-(3,4-dichlorobenzylthio)benzoic acid

ID: ALA1910967

PubChem CID: 54758003

Max Phase: Preclinical

Molecular Formula: C22H15Cl2NO2S

Molecular Weight: 428.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cccc(C#Cc2ccc(C(=O)O)c(SCc3ccc(Cl)c(Cl)c3)c2)c1

Standard InChI:  InChI=1S/C22H15Cl2NO2S/c23-19-9-7-16(11-20(19)24)13-28-21-12-15(6-8-18(21)22(26)27)5-4-14-2-1-3-17(25)10-14/h1-3,6-12H,13,25H2,(H,26,27)

Standard InChI Key:  VOKUNEUMASWNEC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   11.9402   -6.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9391   -6.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6539   -7.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3703   -6.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3675   -6.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6521   -5.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0804   -5.7103    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.7964   -6.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5093   -5.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2237   -6.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9362   -5.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9335   -4.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2125   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5030   -4.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0855   -7.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0867   -8.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7993   -6.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6520   -6.1138    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.6459   -4.4616    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.2254   -5.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5133   -5.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8012   -4.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8100   -4.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0987   -3.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3809   -4.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3788   -4.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0906   -5.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6634   -5.2928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
 14  9  1  0
  5  7  1  0
  4 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  1  0
 15 17  1  0
 11 18  1  0
  8  9  1  0
 12 19  1  0
  4  5  1  0
  1 20  1  0
  9 10  2  0
 20 21  3  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
 11 12  2  0
 24 25  2  0
  6  1  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
 27 22  1  0
  1  2  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1910967

   4-[2-(3-Aminophenyl)ethynyl]-2-[(3,4-dichlorophenyl)methylsulfanyl]benzoic 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: 428.34

Molecular Weight (Monoisotopic): 427.0201

AlogP: 5.97

#Rotatable Bonds: 4

Polar Surface Area: 63.32

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.29

CX Basic pKa: 4.02

CX LogP: 5.60

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.31

Np Likeness Score: -1.11

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