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

ID: ALA4460560

PubChem CID: 141523781

Max Phase: Preclinical

Molecular Formula: C21H27N9O2

Molecular Weight: 437.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCCC(n2nc(-c3cc(N4CCOCC4)n(C)n3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C21H27N9O2/c1-3-17(31)29-6-4-5-14(12-29)30-21-18(20(22)23-13-24-21)19(26-30)15-11-16(27(2)25-15)28-7-9-32-10-8-28/h3,11,13-14H,1,4-10,12H2,2H3,(H2,22,23,24)

Standard InChI Key:  OSPBHLWSQHFCKU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    2.7473  -19.9345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7462  -20.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542  -21.1630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524  -19.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1610  -19.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1659  -20.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9503  -21.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4303  -20.3350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9424  -19.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500  -18.7084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925  -18.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9682  -18.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9634  -17.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846  -17.5717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083  -18.2357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9275  -16.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6240  -17.3384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3726  -17.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0291  -17.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9431  -16.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1945  -16.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320  -16.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085  -21.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6631  -22.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172  -23.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7170  -23.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2623  -22.7227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0079  -21.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0621  -22.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3165  -23.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6074  -22.2821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1162  -23.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 11  2  0
  9 11  1  0
 14 16  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 13 17  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
  7 23  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4460560

   ---

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: 437.51

Molecular Weight (Monoisotopic): 437.2288

AlogP: 1.00

#Rotatable Bonds: 4

Polar Surface Area: 120.22

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.92

CX LogP: 0.92

CX LogD: 0.92

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -1.13

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