7-[[4-[4-[[(3R,4R)-3-aminotetrahydropyran-4-yl]amino]-3-methyl-pyrazol-1-yl]pyrimidin-2-yl]amino]-N,3-dimethyl-imidazo[1,5-a]pyridine-1-carboxamide

ID: ALA4741959

PubChem CID: 162647292

Max Phase: Preclinical

Molecular Formula: C23H28N10O2

Molecular Weight: 476.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1nc(C)n2ccc(Nc3nccc(-n4cc(N[C@@H]5CCOC[C@@H]5N)c(C)n4)n3)cc12

Standard InChI:  InChI=1S/C23H28N10O2/c1-13-18(29-17-6-9-35-12-16(17)24)11-33(31-13)20-4-7-26-23(30-20)28-15-5-8-32-14(2)27-21(19(32)10-15)22(34)25-3/h4-5,7-8,10-11,16-17,29H,6,9,12,24H2,1-3H3,(H,25,34)(H,26,28,30)/t16-,17+/m0/s1

Standard InChI Key:  NPSUYJDNOFYGMK-DLBZAZTESA-N

Molfile:  

 
     RDKit          2D

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    3.8163  -28.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151  -29.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232  -30.0778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328  -29.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2300  -28.8457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9412  -30.0758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3549  -30.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0599  -29.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6435  -28.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3489  -28.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0635  -28.8589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6765  -28.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3406  -27.5530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0247  -26.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5189  -27.6232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791  -27.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9243  -26.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070  -26.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569  -27.1449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4026  -25.7020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680  -24.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5463  -24.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2149  -23.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4020  -23.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215  -24.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2539  -24.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3590  -24.3818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247  -25.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
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 14 15  2  0
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 16 12  2  0
 14 17  1  0
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 18 19  1  0
 18 20  2  0
 19 21  1  0
  6 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 22  1  0
 24 27  1  0
 28 27  1  6
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 29 34  1  6
 25 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741959

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 476.55

Molecular Weight (Monoisotopic): 476.2397

AlogP: 1.56

#Rotatable Bonds: 6

Polar Surface Area: 149.31

Molecular Species: BASE

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.17

CX Basic pKa: 9.20

CX LogP: -0.45

CX LogD: -2.15

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.33

Np Likeness Score: -1.20

References

1. Barlaam B,Boiko S,Boyd S,Dry H,Gingipalli L,Ikeda T,Johnson T,Kawatkar S,Lorthioir O,Pike A,Pollard H,Read J,Su Q,Wang H,Wang H,Wang L,Wang P,Edmondson SD.  (2020)  Novel potent and selective pyrazolylpyrimidine-based SYK inhibitors.,  30  (22): [PMID:32877741] [10.1016/j.bmcl.2020.127523]

Source

Source(1):

• Scientific Literature