2-(4-(6-ethynyl-9H-purin-2-ylamino)phenyl)acetamide

ID: ALA4776060

PubChem CID: 162642974

Max Phase: Preclinical

Molecular Formula: C15H12N6O

Molecular Weight: 292.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#Cc1nc(Nc2ccc(CC(N)=O)cc2)nc2[nH]cnc12

Standard InChI:  InChI=1S/C15H12N6O/c1-2-11-13-14(18-8-17-13)21-15(20-11)19-10-5-3-9(4-6-10)7-12(16)22/h1,3-6,8H,7H2,(H2,16,22)(H2,17,18,19,20,21)

Standard InChI Key:  PNAPIWWSSSUJJA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   20.7668  -12.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7657  -13.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4737  -13.9114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4719  -12.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1805  -12.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1854  -13.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9697  -13.7523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4497  -13.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9619  -12.4204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4695  -11.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4616  -10.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0576  -13.9105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3502  -13.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3554  -12.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6489  -12.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9399  -12.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9418  -13.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6490  -13.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2319  -12.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5244  -12.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8165  -12.2758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5249  -13.5012    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 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776060

   ---

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: 292.30

Molecular Weight (Monoisotopic): 292.1073

AlogP: 1.11

#Rotatable Bonds: 4

Polar Surface Area: 109.58

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.60

CX Basic pKa: 2.34

CX LogP: 1.19

CX LogD: 1.19

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.62

Np Likeness Score: -1.13

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