2-(5,6-dimethylbenzo[d]thiazol-2-ylamino)-2-oxo-1-phenylethanesulfonic acid

ID: ALA4764055

PubChem CID: 124115346

Max Phase: Preclinical

Molecular Formula: C17H16N2O4S2

Molecular Weight: 376.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc2nc(NC(=O)C(c3ccccc3)S(=O)(=O)O)sc2cc1C

Standard InChI:  InChI=1S/C17H16N2O4S2/c1-10-8-13-14(9-11(10)2)24-17(18-13)19-16(20)15(25(21,22)23)12-6-4-3-5-7-12/h3-9,15H,1-2H3,(H,18,19,20)(H,21,22,23)

Standard InChI Key:  FPIHNPXDRSEKPJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.1231  -10.8422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403  -10.8422    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5317  -10.1345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257  -12.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246  -12.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5326  -13.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423  -12.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395  -12.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5308  -11.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9456  -11.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549  -12.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6487  -10.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3610  -11.6560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0703  -12.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580  -12.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1566  -12.8742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8134  -11.7266    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3625  -12.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9554  -13.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3646  -13.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1808  -13.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5860  -13.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1745  -12.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5925  -14.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4032  -13.0238    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
 21 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764055

   ---

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: 376.46

Molecular Weight (Monoisotopic): 376.0551

AlogP: 3.48

#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: -1.30

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 1.67

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -1.47

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