4-(5-Aminothiazolo[5,4-d]pyrimidin-7-yl)-N-(6-methoxy-2-methyl-3-pyridyl)piperazine-1-carboxamide

ID: ALA4216301

PubChem CID: 145974197

Max Phase: Preclinical

Molecular Formula: C17H20N8O2S

Molecular Weight: 400.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)N2CCN(c3nc(N)nc4scnc34)CC2)c(C)n1

Standard InChI:  InChI=1S/C17H20N8O2S/c1-10-11(3-4-12(20-10)27-2)21-17(26)25-7-5-24(6-8-25)14-13-15(28-9-19-13)23-16(18)22-14/h3-4,9H,5-8H2,1-2H3,(H,21,26)(H2,18,22,23)

Standard InChI Key:  FXHQAAGCIBZXGI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   14.4728   -5.9102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4716   -6.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1797   -7.1387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1779   -5.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8865   -5.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8913   -6.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6757   -6.9795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.1557   -6.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6679   -5.6477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7636   -7.1377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1754   -4.6841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8838   -4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8833   -3.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1762   -3.0502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4679   -3.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4668   -4.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1769   -2.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4695   -1.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8849   -1.8249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5923   -2.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5881   -3.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2946   -3.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0036   -3.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0016   -2.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2945   -1.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2918   -1.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7115   -3.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7120   -4.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
  4 11  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 25 26  1  0
 23 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4216301

   ---

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: 400.47

Molecular Weight (Monoisotopic): 400.1430

AlogP: 1.73

#Rotatable Bonds: 3

Polar Surface Area: 122.39

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.45

CX Basic pKa: 4.37

CX LogP: 1.44

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.82

References

1. Reuberson J, Horsley H, Franklin RJ, Ford D, Neuss J, Brookings D, Huang Q, Vanderhoydonck B, Gao LJ, Jang MY, Herdewijn P, Ghawalkar A, Fallah-Arani F, Khan AR, Henshall J, Jairaj M, Malcolm S, Ward E, Shuttleworth L, Lin Y, Li S, Louat T, Waer M, Herman J, Payne A, Ceska T, Doyle C, Pitt W, Calmiano M, Augustin M, Steinbacher S, Lammens A, Allen R..  (2018)  Discovery of a Potent, Orally Bioavailable PI4KIIIβ Inhibitor (UCB9608) Able To Significantly Prolong Allogeneic Organ Engraftment in Vivo.,  61  (15): [PMID:29952567] [10.1021/acs.jmedchem.8b00521]

Source

Source(1):

• Scientific Literature