2-(benzo[d]thiazol-2-ylamino)-1-(4-bromophenyl)-2-oxoethanesulfonic acid

ID: ALA4762502

PubChem CID: 124115261

Max Phase: Preclinical

Molecular Formula: C15H11BrN2O4S2

Molecular Weight: 427.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2ccccc2s1)C(c1ccc(Br)cc1)S(=O)(=O)O

Standard InChI:  InChI=1S/C15H11BrN2O4S2/c16-10-7-5-9(6-8-10)13(24(20,21)22)14(19)18-15-17-11-3-1-2-4-12(11)23-15/h1-8,13H,(H,17,18,19)(H,20,21,22)

Standard InChI Key:  INFMQQLKKJMTEL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   36.6126   -3.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4298   -3.4504    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.0212   -2.7427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3153   -4.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3141   -5.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0222   -5.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7318   -5.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7290   -4.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0204   -4.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4352   -4.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1444   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1383   -3.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8506   -4.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5598   -4.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1475   -5.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6462   -5.4823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3029   -4.3348    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   40.8521   -4.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4449   -5.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8541   -6.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6703   -6.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0756   -5.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6640   -4.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6061   -5.9119    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 10  2  1  0
  2 12  1  0
 11 13  1  0
 13 14  1  0
 11 15  2  0
 14 16  2  0
 16 19  1  0
 18 17  1  0
 17 14  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762502

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 427.30

Molecular Weight (Monoisotopic): 425.9344

AlogP: 3.63

#Rotatable Bonds: 4

Polar Surface Area: 96.36

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.61

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 1.41

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: -1.55

References

1. He R,Wang J,Yu ZH,Zhang RY,Liu S,Wu L,Zhang ZY.  (2016)  Inhibition of Low Molecular Weight Protein Tyrosine Phosphatase by an Induced-Fit Mechanism.,  59  (19.0): [PMID:27676368] [10.1021/acs.jmedchem.6b00993]

2. Forghieri, Marco M and 8 more authors.  2009-04-01  Synthesis, activity and molecular modeling of a new series of chromones as low molecular weight protein tyrosine phosphatase inhibitors.  [PMID:19297174]

3. He, Yantao Y and 11 more authors.  2013-06-27  A potent and selective small-molecule inhibitor for the lymphoid-specific tyrosine phosphatase (LYP), a target associated with autoimmune diseases.  [PMID:23713581]

4. He, Rongjun R and 6 more authors.  2016-10-13  Inhibition of Low Molecular Weight Protein Tyrosine Phosphatase by an Induced-Fit Mechanism.  [PMID:27676368]

Source

Source(1):

• Scientific Literature