2-(4-methoxybenzo[d]thiazol-2-ylamino)-2-oxo-1-phenylethanesulfonic acid

ID: ALA4783253

PubChem CID: 124115336

Max Phase: Preclinical

Molecular Formula: C16H14N2O5S2

Molecular Weight: 378.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc2sc(NC(=O)C(c3ccccc3)S(=O)(=O)O)nc12

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

Standard InChI Key:  ZQGVENSHMGOPGV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.3088   -3.5123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260   -3.5123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7174   -2.8046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115   -4.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103   -5.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184   -5.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4280   -5.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4252   -4.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166   -4.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1314   -4.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8406   -4.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8344   -3.1030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5468   -4.3261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2560   -4.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8437   -5.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -5.5442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9991   -4.3967    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5483   -5.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1411   -5.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5503   -6.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3665   -6.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7718   -5.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3602   -4.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1436   -7.1226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3264   -7.1247    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
 20 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4783253

   ---

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: -1.05

CX Basic pKa: ┄

CX LogP: 1.69

CX LogD: 0.50

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: -1.35

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