2-(benzo[d]thiazol-2-ylamino)-1-(3-nitrophenyl)-2-oxoethanesulfonic acid

ID: ALA4777881

PubChem CID: 162644170

Max Phase: Preclinical

Molecular Formula: C15H11N3O6S2

Molecular Weight: 393.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2ccccc2s1)C(c1cccc([N+](=O)[O-])c1)S(=O)(=O)O

Standard InChI:  InChI=1S/C15H11N3O6S2/c19-14(17-15-16-11-6-1-2-7-12(11)25-15)13(26(22,23)24)9-4-3-5-10(8-9)18(20)21/h1-8,13H,(H,16,17,19)(H,22,23,24)

Standard InChI Key:  OAXWIHLMJYKOAU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   25.1224   -3.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9396   -3.5907    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.5310   -2.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8251   -4.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8239   -5.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5320   -6.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2416   -5.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2388   -4.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5302   -4.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9450   -4.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6542   -4.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6481   -3.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3604   -4.4045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0696   -4.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6573   -5.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1560   -5.6226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8127   -4.4751    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.3619   -5.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9547   -5.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3639   -6.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1801   -6.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5854   -5.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1738   -5.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1166   -4.4165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4090   -4.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1164   -3.5993    0.0000 O   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  2  0
 24 26  1  0
  4 24  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4777881

   ---

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: 393.40

Molecular Weight (Monoisotopic): 393.0089

AlogP: 2.77

#Rotatable Bonds: 5

Polar Surface Area: 139.50

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.64

CX Basic pKa: ┄

CX LogP: 1.51

CX LogD: 0.58

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.39

Np Likeness Score: -1.78

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