rac-6-[1-[1-(2-Pyridyl)pyrazol-3-yl]ethyl]-3H-1,3-benzothiazol-2-one

ID: ALA3823222

PubChem CID: 127052040

Max Phase: Preclinical

Molecular Formula: C17H14N4OS

Molecular Weight: 322.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(c1ccc2[nH]c(=O)sc2c1)c1ccn(-c2ccccn2)n1

Standard InChI:  InChI=1S/C17H14N4OS/c1-11(12-5-6-14-15(10-12)23-17(22)19-14)13-7-9-21(20-13)16-4-2-3-8-18-16/h2-11H,1H3,(H,19,22)

Standard InChI Key:  CPNJIZRYNQHWHQ-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 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 C   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  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  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:

   

   ALA3823222

   ---

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: 322.39

Molecular Weight (Monoisotopic): 322.0888

AlogP: 3.32

#Rotatable Bonds: 3

Polar Surface Area: 63.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.29

CX Basic pKa: 1.82

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: -1.64

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