3-(2-fluoro-phenyl)-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-7-pyrazin-1-yl-pyrazolo[1,5-d][1,2,4]triazine

ID: ALA212637

PubChem CID: 44413421

Max Phase: Preclinical

Molecular Formula: C19H15FN9O+

Molecular Weight: 404.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ncnc1COc1nn2c(-[n+]3ccncc3)nncc2c1-c1ccccc1F

Standard InChI:  InChI=1S/C19H15FN9O/c1-27-16(22-12-24-27)11-30-18-17(13-4-2-3-5-14(13)20)15-10-23-25-19(29(15)26-18)28-8-6-21-7-9-28/h2-10,12H,11H2,1H3/q+1

Standard InChI Key:  YCTZWWGYTRDQQM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    9.0420   -9.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2254   -9.1672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1082   -9.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8488  -10.3478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4237   -9.7558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2401   -9.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7486   -4.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1798   -5.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1767   -4.7450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4584   -4.3362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4604   -5.9897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7459   -5.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1294   -6.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4627   -6.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2853   -6.7978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0474   -7.5941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4133   -5.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4161   -4.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7010   -4.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9868   -4.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921   -5.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7077   -6.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8948   -5.9881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8934   -6.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6075   -7.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3227   -6.8117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3193   -5.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6046   -5.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4572   -8.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7153   -6.9582    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 11  1  0
  2  3  1  0
 14 16  1  0
 11  8  1  0
 13 17  1  0
  3  4  2  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
 10  7  2  0
 21 22  2  0
 22 17  1  0
 11 12  1  0
  8 23  1  0
  5  1  1  0
 23 24  2  0
 24 25  1  0
  5  6  1  0
 25 26  2  0
  1  2  2  0
 26 27  1  0
  7 12  1  0
 27 28  2  0
 28 23  1  0
 12 13  2  0
 16 29  1  0
 29  1  1  0
 13 14  1  0
 22 30  1  0
M  CHG  1  23   1
M  END

Alternative Forms

1. Parent:

   

   ALA212637

   3-(2-Fluorophenyl)-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-7-pyrazin-1-ium-1-ylpyrazolo[1,5-d][1,2,4]triazine

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: 404.39

Molecular Weight (Monoisotopic): 404.1378

AlogP: 1.31

#Rotatable Bonds: 5

Polar Surface Area: 99.79

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.54

CX LogP: -1.56

CX LogD: -1.56

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -1.35

References

1. Carling RW, Russell MG, Moore KW, Mitchinson A, Guiblin A, Smith A, Wafford KA, Marshall G, Atack JR, Street LJ..  (2006)  2,3,7-Trisubstituted pyrazolo[1,5-d][1,2,4]triazines: functionally selective GABAA alpha3-subtype agonists.,  16  (13): [PMID:16621541] [10.1016/j.bmcl.2006.03.081]

Source

Source(1):

• Scientific Literature