1-(3-((4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)piperidin-1-yl)prop-2-en-1-one

ID: ALA4517080

PubChem CID: 141523774

Max Phase: Preclinical

Molecular Formula: C14H17BrN6O

Molecular Weight: 365.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCCC(Cn2nc(Br)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C14H17BrN6O/c1-2-10(22)20-5-3-4-9(6-20)7-21-14-11(12(15)19-21)13(16)17-8-18-14/h2,8-9H,1,3-7H2,(H2,16,17,18)

Standard InChI Key:  JUKXZGJYTMCCBR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   13.2717  -20.4050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2706  -21.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9786  -21.6335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9769  -19.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6855  -20.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6903  -21.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4747  -21.4744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9547  -20.8055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4669  -20.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9744  -19.1789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7148  -19.3638    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.7317  -22.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5320  -22.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7848  -23.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5812  -23.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1279  -22.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8724  -21.9743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0703  -21.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4177  -21.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2175  -21.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1633  -20.5891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7628  -20.9251    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
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4517080

   ---

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: 365.24

Molecular Weight (Monoisotopic): 364.0647

AlogP: 1.60

#Rotatable Bonds: 3

Polar Surface Area: 89.93

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.40

CX LogP: 1.12

CX LogD: 1.12

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: -0.87

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