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

ID: ALA4762007

PubChem CID: 124115262

Max Phase: Preclinical

Molecular Formula: C15H11ClN2O4S2

Molecular Weight: 382.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2ccccc2s1)C(c1ccccc1Cl)S(=O)(=O)O

Standard InChI:  InChI=1S/C15H11ClN2O4S2/c16-10-6-2-1-5-9(10)13(24(20,21)22)14(19)18-15-17-11-7-3-4-8-12(11)23-15/h1-8,13H,(H,17,18,19)(H,20,21,22)

Standard InChI Key:  CVWIJCOYNULQSI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.4504   -9.9136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2676   -9.9136    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590   -9.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1530  -11.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1519  -11.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599  -12.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696  -11.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667  -11.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581  -10.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2729  -10.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9821  -11.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9760   -9.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6883  -10.7274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3975  -11.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852  -11.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4839  -11.9455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1406  -10.7980    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6898  -11.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2827  -12.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6919  -12.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5080  -12.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9133  -12.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5018  -11.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557   -9.9216    0.0000 Cl  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
  9 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762007

   ---

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: 382.85

Molecular Weight (Monoisotopic): 381.9849

AlogP: 3.52

#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: -1.60

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 1.25

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -1.68

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