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

ID: ALA4741385

PubChem CID: 124115348

Max Phase: Preclinical

Molecular Formula: C18H16N2O6S2

Molecular Weight: 420.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc2nc(NC(=O)C(c3ccccc3)S(=O)(=O)O)sc2c1

Standard InChI:  InChI=1S/C18H16N2O6S2/c1-2-26-17(22)12-8-9-13-14(10-12)27-18(19-13)20-16(21)15(28(23,24)25)11-6-4-3-5-7-11/h3-10,15H,2H2,1H3,(H,19,20,21)(H,23,24,25)

Standard InChI Key:  XUJANKCEYXKBAF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   25.1142  -18.4817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9314  -18.4817    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.5228  -17.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8168  -19.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8157  -20.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5237  -20.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2334  -20.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2306  -19.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5219  -19.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9367  -19.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6460  -19.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6398  -18.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3521  -19.2955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0614  -19.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6490  -20.5240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1477  -20.5137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8045  -19.3661    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.3536  -19.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9465  -20.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3557  -21.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1719  -21.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5771  -20.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1656  -19.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3966  -20.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8099  -21.3681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8005  -19.9527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6271  -21.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0404  -22.0676    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
 24 25  1  0
 24 26  2  0
 22 24  1  0
 25 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741385

   ---

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: 420.47

Molecular Weight (Monoisotopic): 420.0450

AlogP: 3.04

#Rotatable Bonds: 6

Polar Surface Area: 122.66

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.61

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 1.00

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: -1.41

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