2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-oxo-1-phenylethanesulfonic acid

ID: ALA4762141

PubChem CID: 124115342

Max Phase: Preclinical

Molecular Formula: C16H14N2O5S2

Molecular Weight: 378.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2nc(NC(=O)C(c3ccccc3)S(=O)(=O)O)sc2c1

Standard InChI:  InChI=1S/C16H14N2O5S2/c1-23-11-7-8-12-13(9-11)24-16(17-12)18-15(19)14(25(20,21)22)10-5-3-2-4-6-10/h2-9,14H,1H3,(H,17,18,19)(H,20,21,22)

Standard InChI Key:  WMQYIEOKGALPGV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   24.5240   -9.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3412   -9.4802    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.9326   -8.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2266  -10.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2255  -11.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9335  -11.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6432  -11.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6404  -10.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9317  -10.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3465  -10.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0558  -10.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0496   -9.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7619  -10.2941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4712  -10.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0588  -11.5225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5575  -11.5122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2143  -10.3647    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.7634  -10.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3563  -11.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7655  -12.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5817  -12.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9869  -11.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5754  -10.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8041  -11.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2174  -12.3668    0.0000 C   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
 22 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762141

   ---

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: 378.43

Molecular Weight (Monoisotopic): 378.0344

AlogP: 2.87

#Rotatable Bonds: 5

Polar Surface Area: 105.59

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.41

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: 0.49

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: -1.45

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