N,1-dimethyl-5-[[4-[3-methyl-4-[(3S)-pyrrolidin-3-yl]oxy-pyrazol-1-yl]pyrimidin-2-yl]amino]indazole-3-carboxamide

ID: ALA4760470

PubChem CID: 162658022

Max Phase: Preclinical

Molecular Formula: C22H25N9O2

Molecular Weight: 447.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1nn(C)c2ccc(Nc3nccc(-n4cc(O[C@H]5CCNC5)c(C)n4)n3)cc12

Standard InChI:  InChI=1S/C22H25N9O2/c1-13-18(33-15-6-8-24-11-15)12-31(28-13)19-7-9-25-22(27-19)26-14-4-5-17-16(10-14)20(21(32)23-2)29-30(17)3/h4-5,7,9-10,12,15,24H,6,8,11H2,1-3H3,(H,23,32)(H,25,26,27)/t15-/m0/s1

Standard InChI Key:  DUQRGTCLMVTXDF-HNNXBMFYSA-N

Molfile:  

 
     RDKit          2D

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   21.5468  -28.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5457  -29.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2537  -29.5619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9634  -29.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9606  -28.3298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2520  -27.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6718  -29.5599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3788  -29.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0838  -29.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7904  -29.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3726  -28.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0763  -27.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7857  -28.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3931  -27.7833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0591  -27.0360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2452  -27.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6975  -26.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9488  -25.7389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8984  -26.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7479  -25.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1927  -27.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2495  -27.1073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9097  -26.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6548  -25.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8376  -25.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5875  -26.6290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1332  -25.1861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3552  -25.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7986  -24.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2021  -23.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6535  -23.1240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9079  -23.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9958  -24.2711    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
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 13  2  0
 12 11  2  0
 11  8  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 14 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
 25 28  1  0
 29 27  1  1
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4760470

   ---

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: 447.50

Molecular Weight (Monoisotopic): 447.2131

AlogP: 1.70

#Rotatable Bonds: 6

Polar Surface Area: 123.81

Molecular Species: BASE

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.70

CX Basic pKa: 10.22

CX LogP: 1.31

CX LogD: -1.37

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -1.43

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