1-(3-(4-amino-3-(5-(2-hydroxypropan-2-yl)-1-methyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-en-1-one

ID: ALA4557416

PubChem CID: 155554605

Max Phase: Preclinical

Molecular Formula: C19H24N8O2

Molecular Weight: 396.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCC(n2nc(-c3cc(C(C)(C)O)n(C)n3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C19H24N8O2/c1-5-14(28)26-7-6-11(9-26)27-18-15(17(20)21-10-22-18)16(24-27)12-8-13(19(2,3)29)25(4)23-12/h5,8,10-11,29H,1,6-7,9H2,2-4H3,(H2,20,21,22)

Standard InChI Key:  BZAVHUAPRBYWRZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   15.7041  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1168  -15.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5252  -15.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2441  -18.5725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2429  -19.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9510  -19.8010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9492  -18.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6578  -18.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6626  -19.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4470  -19.6419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9270  -18.9730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4392  -18.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9467  -17.3464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6892  -17.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4649  -17.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4601  -16.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6814  -16.2097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2051  -16.8737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4242  -15.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7041  -20.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8669  -16.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2296  -21.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7138  -21.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4896  -21.4803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4847  -20.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1535  -21.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0729  -22.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8981  -21.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5620  -22.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  7 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 14  2  0
 12 14  1  0
 17 19  1  0
 10 20  1  0
 16  2  1  0
  2 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 20  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557416

   ---

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: 396.46

Molecular Weight (Monoisotopic): 396.2022

AlogP: 1.00

#Rotatable Bonds: 4

Polar Surface Area: 127.98

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.91

CX LogP: 0.28

CX LogD: 0.28

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -0.85

References

1. Yin Y, Chen CJ, Yu RN, Shu L, Zhang TT, Zhang DY..  (2019)  Discovery of novel selective Janus kinase 2 (JAK2) inhibitors bearing a 1H-pyrazolo[3,4-d]pyrimidin-4-amino scaffold.,  27  (8): [PMID:30846405] [10.1016/j.bmc.2019.02.054]

Source

Source(1):

• Scientific Literature