1-(3-(6-ethynyl-9H-purin-2-ylamino)phenyl)propan-2-one

ID: ALA4776787

PubChem CID: 162643872

Max Phase: Preclinical

Molecular Formula: C16H13N5O

Molecular Weight: 291.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#Cc1nc(Nc2cccc(CC(C)=O)c2)nc2[nH]cnc12

Standard InChI:  InChI=1S/C16H13N5O/c1-3-13-14-15(18-9-17-14)21-16(20-13)19-12-6-4-5-11(8-12)7-10(2)22/h1,4-6,8-9H,7H2,2H3,(H2,17,18,19,20,21)

Standard InChI Key:  GBVGEGLYPVSUGT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.3904   -8.8983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3893   -9.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0973  -10.1268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0956   -8.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -8.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8090   -9.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5934   -9.9677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0734   -9.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5856   -8.6358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0931   -7.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0852   -6.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6813  -10.1258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9739   -9.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9791   -8.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725   -8.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726  -10.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663   -9.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677   -8.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8589  -10.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1509   -9.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435  -10.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -8.9043    0.0000 O   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
 10 11  3  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 18  2  0
 17 16  2  0
 16 13  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776787

   ---

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: 291.31

Molecular Weight (Monoisotopic): 291.1120

AlogP: 2.21

#Rotatable Bonds: 4

Polar Surface Area: 83.56

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.60

CX Basic pKa: 2.32

CX LogP: 2.33

CX LogD: 2.32

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.72

Np Likeness Score: -0.87

References

1. Matheson, Christopher J., Coxon, Christopher R., Bayliss, Richard, Boxall, Kathy, Carbain, Benoit, Fry, Andrew M., Hardcastle, Ian R., Harnor, Suzannah J., Mas-Droux, Corine, Newell, David R., Richards, Mark W., Sivaprakasam, Mangaleswaran, Turner, David, Griffin, Roger J., Golding, Bernard T., Cano, Celine.  (2020)  2-Arylamino-6-ethynylpurines are cysteine-targeting irreversible inhibitors of Nek2 kinase,  11  (6): [PMID:33479670] [10.1039/d0md00074d]

Source

Source(1):

• Scientific Literature