(3R)-4-(6-Amino-1-methyl-pyrazolo[3,4-d]pyrimidin-4-yl)-N-(4-methoxy-2-methyl-phenyl)-3-methyl-piperazine-1-carboxamide

ID: ALA4215775

Cas Number: 1616414-06-2

PubChem CID: 76282315

Max Phase: Preclinical

Molecular Formula: C20H26N8O2

Molecular Weight: 410.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)N2CCN(c3nc(N)nc4c3cnn4C)[C@H](C)C2)c(C)c1

Standard InChI:  InChI=1S/C20H26N8O2/c1-12-9-14(30-4)5-6-16(12)23-20(29)27-7-8-28(13(2)11-27)18-15-10-22-26(3)17(15)24-19(21)25-18/h5-6,9-10,13H,7-8,11H2,1-4H3,(H,23,29)(H2,21,24,25)/t13-/m1/s1

Standard InChI Key:  WRONAJQPZWDYAR-CYBMUJFWSA-N

Molfile:  

     RDKit          2D

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   38.3584  -19.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1797  -19.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5883  -19.9213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.1797  -20.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3584  -20.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1244  -19.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7158  -19.2164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7158  -20.6345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5883  -18.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8945  -20.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4817  -21.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.2518  -20.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6604  -19.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4817  -19.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8945  -22.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4305  -20.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0178  -21.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6437  -19.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0523  -19.9213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6437  -20.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8224  -20.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4097  -19.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8224  -19.2164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.2310  -21.9002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.8942  -21.4159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5636  -21.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6756  -21.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0523  -18.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1  6  1  0
  7  8  2  0
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  3 10  1  1
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 12 13  2  0
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 15 16  1  0
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 12 17  1  0
 18 19  1  0
 14 18  1  0
  9 11  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 26 27  1  0
 26 28  2  0
 22 27  1  0
 23 28  1  0
 27 29  1  0
 20 30  1  0
  4 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4215775

   (3R)-4-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N-(4-methoxy-2-methylphenyl)-3-methyl-1-piperazinecarboxamide

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: 410.48

Molecular Weight (Monoisotopic): 410.2179

AlogP: 2.01

#Rotatable Bonds: 3

Polar Surface Area: 114.43

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.49

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -2.05

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