1-[4-(5-Aminothiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(3,4-dimethoxyphenyl)ethanone

ID: ALA4215673

PubChem CID: 145973476

Max Phase: Preclinical

Molecular Formula: C19H22N6O3S

Molecular Weight: 414.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC(=O)N2CCN(c3nc(N)nc4scnc34)CC2)cc1OC

Standard InChI:  InChI=1S/C19H22N6O3S/c1-27-13-4-3-12(9-14(13)28-2)10-15(26)24-5-7-25(8-6-24)17-16-18(29-11-21-16)23-19(20)22-17/h3-4,9,11H,5-8,10H2,1-2H3,(H2,20,22,23)

Standard InChI Key:  YAHULMMYPWZTOQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   40.7467  -22.3118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7456  -23.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4536  -23.5403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4518  -21.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1604  -22.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1653  -23.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9496  -23.3811    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.4296  -22.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9418  -22.0493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0375  -23.5393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4494  -21.0857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.1578  -20.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1573  -19.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4502  -19.4518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7419  -19.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7407  -20.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4508  -18.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7434  -18.2254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.1558  -18.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8649  -18.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8654  -19.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5737  -19.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2810  -19.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2756  -18.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5667  -18.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9906  -19.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.9804  -18.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.6909  -18.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9945  -20.6660    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
 23 26  1  0
 24 27  1  0
 27 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4215673

   ---

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: 414.49

Molecular Weight (Monoisotopic): 414.1474

AlogP: 1.58

#Rotatable Bonds: 5

Polar Surface Area: 106.70

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.35

CX LogP: 1.70

CX LogD: 1.70

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: -1.13

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