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

ID: ALA4765174

PubChem CID: 124115333

Max Phase: Preclinical

Molecular Formula: C15H11FN2O4S2

Molecular Weight: 366.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2ccc(F)cc2s1)C(c1ccccc1)S(=O)(=O)O

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

Standard InChI Key:  CQJNRDYVDPGZTH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.8548  -19.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6720  -19.9098    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634  -19.2020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575  -21.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5563  -21.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2644  -22.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9740  -21.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9712  -21.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626  -20.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774  -20.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3866  -21.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804  -19.5005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0928  -20.7236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8020  -21.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3897  -21.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8883  -21.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5451  -20.7942    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0943  -21.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6871  -22.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0963  -22.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9125  -22.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3178  -22.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9062  -21.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1349  -22.0913    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
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4765174

   ---

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: -1.59

CX Basic pKa: ┄

CX LogP: 1.74

CX LogD: 0.79

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