6-[Methyl-[1-(2-pyridyl)pyrazol-3-yl]amino]-3H-1,3-benzothiazol-2-one

ID: ALA3823131

PubChem CID: 127049895

Max Phase: Preclinical

Molecular Formula: C16H12N4OS2

Molecular Weight: 340.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(c1ccc2[nH]c(=O)sc2c1)c1nc(-c2ccccn2)cs1

Standard InChI:  InChI=1S/C16H12N4OS2/c1-20(10-5-6-12-14(8-10)23-16(21)19-12)15-18-13(9-22-15)11-4-2-3-7-17-11/h2-9H,1H3,(H,19,21)

Standard InChI Key:  CRPQUNBPUQJQJE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -7.2652    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2729    1.3327    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0380   -0.7567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5020   -1.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319    2.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0984   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2995   -3.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9975   -5.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4963   -5.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2971   -3.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5991   -2.5154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  2  0
 15 19  1  0
 18 16  1  0
 16 17  2  0
 17  8  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3823131

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 340.43

Molecular Weight (Monoisotopic): 340.0453

AlogP: 3.88

#Rotatable Bonds: 3

Polar Surface Area: 61.88

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.73

CX Basic pKa: 1.18

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.61

Np Likeness Score: -1.69

References

1. Gardinier KM, Gernert DL, Porter WJ, Reel JK, Ornstein PL, Spinazze P, Stevens FC, Hahn P, Hollinshead SP, Mayhugh D, Schkeryantz J, Khilevich A, De Frutos O, Gleason SD, Kato AS, Luffer-Atlas D, Desai PV, Swanson S, Burris KD, Ding C, Heinz BA, Need AB, Barth VN, Stephenson GA, Diseroad BA, Woods TA, Yu H, Bredt D, Witkin JM..  (2016)  Discovery of the First α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptor Antagonist Dependent upon Transmembrane AMPA Receptor Regulatory Protein (TARP) γ-8.,  59  (10): [PMID:27067148] [10.1021/acs.jmedchem.6b00125]

Source

Source(1):

• Scientific Literature