2-(benzo[d]thiazol-2-ylamino)-2-oxo-1-p-tolylethanesulfonic acid

ID: ALA4757962

PubChem CID: 162657138

Max Phase: Preclinical

Molecular Formula: C16H14N2O4S2

Molecular Weight: 362.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(C(=O)Nc2nc3ccccc3s2)S(=O)(=O)O)cc1

Standard InChI:  InChI=1S/C16H14N2O4S2/c1-10-6-8-11(9-7-10)14(24(20,21)22)15(19)18-16-17-12-4-2-3-5-13(12)23-16/h2-9,14H,1H3,(H,17,18,19)(H,20,21,22)

Standard InChI Key:  CGIHSSPGGIXHSI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   25.0812  -18.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8984  -18.3290    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.4898  -17.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7838  -19.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7827  -20.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4907  -20.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2004  -20.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1975  -19.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4889  -19.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9037  -19.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6129  -19.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6068  -17.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3191  -19.1428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0283  -19.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6160  -20.3713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1147  -20.3610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7714  -19.2134    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.3206  -19.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9135  -20.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3227  -21.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1388  -21.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5441  -20.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1326  -19.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0746  -20.7906    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
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757962

   ---

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: 362.43

Molecular Weight (Monoisotopic): 362.0395

AlogP: 3.17

#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: -1.26

CX Basic pKa: ┄

CX LogP: 2.48

CX LogD: 1.15

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: -1.55

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