2-(benzo[d]thiazol-2-ylamino)-1-(3-fluorophenyl)-2-oxoethanesulfonic acid

ID: ALA4782212

PubChem CID: 162665017

Max Phase: Preclinical

Molecular Formula: C15H11FN2O4S2

Molecular Weight: 366.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2ccccc2s1)C(c1cccc(F)c1)S(=O)(=O)O

Standard InChI:  InChI=1S/C15H11FN2O4S2/c16-10-5-3-4-9(8-10)13(24(20,21)22)14(19)18-15-17-11-6-1-2-7-12(11)23-15/h1-8,13H,(H,17,18,19)(H,20,21,22)

Standard InChI Key:  HQCSHUQDPNFFCY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   14.6764   -3.9332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4936   -3.9332    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0850   -3.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3791   -5.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779   -5.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0860   -6.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7956   -5.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7928   -5.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0842   -4.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4990   -4.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2082   -5.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2020   -3.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9144   -4.7471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6236   -5.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2113   -5.9755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7099   -5.9652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3667   -4.8177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9159   -5.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5087   -6.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9179   -6.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7341   -6.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1394   -6.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7278   -5.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6713   -4.7588    0.0000 F   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
  4 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4782212

   ---

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: 366.39

Molecular Weight (Monoisotopic): 366.0144

AlogP: 3.00

#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: 1.74

CX LogD: 0.78

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: -1.82

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