[4-(5-Aminothiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-(1H-indol-2-yl)methanone

ID: ALA4218178

PubChem CID: 145969385

Max Phase: Preclinical

Molecular Formula: C18H17N7OS

Molecular Weight: 379.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2CCN(C(=O)c3cc4ccccc4[nH]3)CC2)c2ncsc2n1

Standard InChI:  InChI=1S/C18H17N7OS/c19-18-22-15(14-16(23-18)27-10-20-14)24-5-7-25(8-6-24)17(26)13-9-11-3-1-2-4-12(11)21-13/h1-4,9-10,21H,5-8H2,(H2,19,22,23)

Standard InChI Key:  WPPOSOGWMNQIDJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   29.8632  -23.0258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8621  -23.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5701  -24.2543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5683  -22.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2769  -23.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2818  -23.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0661  -24.0952    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.5461  -23.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0583  -22.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1540  -24.2533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5659  -21.7997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2743  -21.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2738  -20.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5667  -20.1658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8584  -20.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8572  -21.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5673  -19.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8599  -18.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2723  -18.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0185  -19.2713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3584  -18.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1578  -17.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5633  -18.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3748  -18.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7869  -17.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3814  -17.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5637  -17.2511    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
 19 20  1  0
 20 23  1  0
 22 21  1  0
 21 19  2  0
 17 19  1  0
 22 23  2  0
 22 27  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4218178

   ---

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: 379.45

Molecular Weight (Monoisotopic): 379.1215

AlogP: 2.11

#Rotatable Bonds: 2

Polar Surface Area: 104.03

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.35

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -1.50

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