N-(4-morpholinophenyl)-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine

ID: ALA1956687

PubChem CID: 135979614

Max Phase: Preclinical

Molecular Formula: C18H18N8O

Molecular Weight: 362.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1

Standard InChI:  InChI=1S/C18H18N8O/c1-3-15(25-5-7-27-8-6-25)4-2-14(1)24-17-18-20-12-23-26(18)16(11-19-17)13-9-21-22-10-13/h1-4,9-12H,5-8H2,(H,19,24)(H,21,22)

Standard InChI Key:  WSPYBPVYCFYIRM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    1.8150   -0.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    0.0565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5297    0.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8132    1.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991    0.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004    0.8863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3112    1.1440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    0.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3092   -0.1992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8148   -1.1837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5247   -1.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5215   -2.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2306   -2.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419   -2.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2301   -1.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578   -2.8286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6558   -3.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675   -4.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0853   -3.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867   -2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3703   -2.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114    2.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4825    2.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254    3.3991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3991    3.3973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456    2.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  2  3  1  0
 13 14  2  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
  6  7  1  0
 14 17  1  0
 17 18  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
  4  6  1  0
  1 10  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  5  6  1  0
  4 23  1  0
 23 24  1  0
 10 11  1  0
  1  2  2  0
 11 12  2  0
  5  1  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1956687

   ---

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: 362.40

Molecular Weight (Monoisotopic): 362.1604

AlogP: 2.09

#Rotatable Bonds: 4

Polar Surface Area: 96.26

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.81

CX Basic pKa: 2.54

CX LogP: 1.74

CX LogD: 1.74

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -2.09

References

1. Andrews MJ, Clase JA, Bar G, Tricarico G, Edwards PJ, Brys R, Chambers M, Schmidt W, MacLeod A, Hirst K, Allen V, Birault V, Le J, Harris J, Self A, Nash K, Dixon G..  (2012)  Discovery of a series of imidazopyrazine small molecule inhibitors of the kinase MAPKAPK5, that show activity using in vitro and in vivo models of rheumatoid arthritis.,  22  (6): [PMID:22342143] [10.1016/j.bmcl.2012.01.077]

Source

Source(1):

• Scientific Literature