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

ID: ALA4763433

PubChem CID: 155925934

Max Phase: Preclinical

Molecular Formula: C22H26N10O2

Molecular Weight: 462.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1nc(C)n2ccc(Nc3nccc(-n4cc(N[C@@H]5CCOC[C@@H]5N)cn4)n3)cc12

Standard InChI:  InChI=1S/C22H26N10O2/c1-13-27-20(21(33)24-2)18-9-14(4-7-31(13)18)29-22-25-6-3-19(30-22)32-11-15(10-26-32)28-17-5-8-34-12-16(17)23/h3-4,6-7,9-11,16-17,28H,5,8,12,23H2,1-2H3,(H,24,33)(H,25,29,30)/t16-,17+/m0/s1

Standard InChI Key:  OALOIHPPRINPBM-DLBZAZTESA-N

Molfile:  

 
     RDKit          2D

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    3.2632  -18.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2621  -19.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9701  -19.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798  -19.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770  -18.4492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683  -18.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3881  -19.6793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8019  -19.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5068  -19.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905  -18.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7959  -18.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5105  -18.4624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1234  -17.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876  -17.1566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9672  -17.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6724  -15.8588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6209  -16.8063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4717  -15.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9659  -17.2268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261  -16.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3712  -15.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5540  -15.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039  -16.7485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8496  -15.3055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5150  -14.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9932  -13.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6618  -13.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8490  -13.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3685  -13.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7008  -14.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8060  -13.9853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  8 11  2  0
  9 10  2  0
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 12 11  1  0
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 15 16  1  0
 16 12  2  0
 14 17  1  0
 16 18  1  0
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4763433

   ---

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: 462.52

Molecular Weight (Monoisotopic): 462.2240

AlogP: 1.25

#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: 11.16

CX Basic pKa: 9.20

CX LogP: -0.58

CX LogD: -2.28

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -1.24

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