3-(5-Aminothiazolo[5,4-d]pyrimidin-7-yl)-N-(4-methoxyphenyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxamide

ID: ALA4217771

PubChem CID: 145974272

Max Phase: Preclinical

Molecular Formula: C19H21N7O2S

Molecular Weight: 411.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)N2C3CCC2CN(c2nc(N)nc4scnc24)C3)cc1

Standard InChI:  InChI=1S/C19H21N7O2S/c1-28-14-6-2-11(3-7-14)22-19(27)26-12-4-5-13(26)9-25(8-12)16-15-17(29-10-21-15)24-18(20)23-16/h2-3,6-7,10,12-13H,4-5,8-9H2,1H3,(H,22,27)(H2,20,23,24)

Standard InChI Key:  QYIQGRIZKFLIBT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.3766  -13.5414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3755  -14.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0877  -14.7823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0859  -13.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8027  -13.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8076  -14.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6002  -14.6190    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.0843  -13.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924  -13.2748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6592  -14.7814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0834  -12.3030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8001  -11.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7996  -11.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0842  -10.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3718  -11.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3706  -11.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0849   -9.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3734   -9.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8011   -9.4149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5168   -9.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5126  -10.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2274  -11.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9405  -10.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9385   -9.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2273   -9.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6567  -11.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6571  -11.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4099  -11.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7578  -11.7337    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
 26 27  1  0
 13 28  1  0
 28 29  1  0
 15 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4217771

   ---

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: 411.49

Molecular Weight (Monoisotopic): 411.1477

AlogP: 2.56

#Rotatable Bonds: 3

Polar Surface Area: 109.50

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 4.35

CX LogP: 2.46

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.68

Np Likeness Score: -1.21

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