5-(8-(4-morpholinophenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)isoindolin-1-one

ID: ALA1956682

PubChem CID: 57345529

Max Phase: Preclinical

Molecular Formula: C23H21N7O2

Molecular Weight: 427.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21

Standard InChI:  InChI=1S/C23H21N7O2/c31-23-19-6-1-15(11-16(19)12-25-23)20-13-24-21(22-26-14-27-30(20)22)28-17-2-4-18(5-3-17)29-7-9-32-10-8-29/h1-6,11,13-14H,7-10,12H2,(H,24,28)(H,25,31)

Standard InChI Key:  ZDLDULHTZCUMMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
    1.4773   -1.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950   -1.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1921   -0.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755   -0.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7612   -1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625   -0.5368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0268   -0.2791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5160   -0.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0289   -1.6225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -2.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871   -3.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839   -3.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8932   -4.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6046   -3.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6025   -3.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927   -2.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -4.2524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3187   -5.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305   -5.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7484   -5.0786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7498   -4.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0333   -3.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737    0.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    1.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518    1.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7568    1.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    2.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1864    1.9362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8021    2.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4651    3.2474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    3.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883    3.7749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 10 11  1  0
 23 24  2  0
 24 28  1  0
  1  2  2  0
 27 25  1  0
 11 12  2  0
 25 26  2  0
 26 23  1  0
 27 28  2  0
  5  1  1  0
 12 13  1  0
  2  3  1  0
 13 14  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 14 15  1  0
 31 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1956682

   5-(8-(4-Morpholinophenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)isoindolin-1-one

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: 427.47

Molecular Weight (Monoisotopic): 427.1757

AlogP: 2.61

#Rotatable Bonds: 4

Polar Surface Area: 96.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: 2.37

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.37

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