6-((2-ethoxyethyl)(4-(pyridin-2-yl)thiazol-2-yl)amino)benzo[d]thiazol-2(3H)-one

ID: ALA3823961

PubChem CID: 127049260

Max Phase: Preclinical

Molecular Formula: C19H18N4O2S2

Molecular Weight: 398.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H18N4O2S2/c1-2-25-10-9-23(13-6-7-15-17(11-13)27-19(24)22-15)18-21-16(12-26-18)14-5-3-4-8-20-14/h3-8,11-12H,2,9-10H2,1H3,(H,22,24)

Standard InChI Key:  RSDXBKWFUNFRRY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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
   -2.3155   -0.7475    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
    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
   -3.6181   -1.4930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153   -0.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0481    0.7432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5143    1.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2688   -0.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2689   -1.3545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6265   -2.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300   -3.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9385   -5.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2420   -5.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2488   -7.1823    0.0000 C   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
   -7.1200    2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3296    3.7023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0365    5.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5357    5.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3279    3.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6210    2.4779    0.0000 C   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
  1  6  1  0
  5  7  1  0
  6  5  2  0
  6  9  1  0
  7  8  1  0
  8  9  1  0
  3 10  1  0
 10 11  1  0
 11 12  2  0
 11 15  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8 21  2  0
 13 22  1  0
 22 23  2  0
 22 27  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3823961

   ---

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: 398.51

Molecular Weight (Monoisotopic): 398.0871

AlogP: 4.28

#Rotatable Bonds: 7

Polar Surface Area: 71.11

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.72

CX Basic pKa: 1.18

CX LogP: 4.51

CX LogD: 4.51

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.47

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