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

ID: ALA4564903

PubChem CID: 155559780

Max Phase: Preclinical

Molecular Formula: C17H20N8O

Molecular Weight: 352.40

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H20N8O/c1-4-13(26)24-6-5-11(8-24)25-17-14(16(18)19-9-20-17)15(22-25)12-7-10(2)23(3)21-12/h4,7,9,11H,1,5-6,8H2,2-3H3,(H2,18,19,20)

Standard InChI Key:  BWCSPBKMOKIKAK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    6.3229   -8.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502  -11.3663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4490  -12.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1571  -12.5949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1553  -10.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8639  -11.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8687  -12.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531  -12.4357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1331  -11.7669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453  -11.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1528  -10.1403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953  -10.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710  -10.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6662   -9.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8875   -9.0036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4112   -9.6676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6303   -8.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9101  -13.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330  -13.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172  -14.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6930  -14.2778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6881  -13.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569  -14.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2763  -15.5674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1015  -14.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7655  -14.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  5 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 10 12  1  0
 15 17  1  0
  8 18  1  0
 14  1  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4564903

   ---

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: 352.40

Molecular Weight (Monoisotopic): 352.1760

AlogP: 1.08

#Rotatable Bonds: 3

Polar Surface Area: 107.75

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.91

CX LogP: 0.63

CX LogD: 0.63

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.22

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