4-(6-ethynyl-9H-purin-2-ylamino)-N-methylbenzamide

ID: ALA4756141

PubChem CID: 162655267

Max Phase: Preclinical

Molecular Formula: C15H12N6O

Molecular Weight: 292.30

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H12N6O/c1-3-11-12-13(18-8-17-12)21-15(20-11)19-10-6-4-9(5-7-10)14(22)16-2/h1,4-8H,2H3,(H,16,22)(H2,17,18,19,20,21)

Standard InChI Key:  CCEQHBDFBPUQRB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.3946   -3.8218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3934   -4.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1015   -5.0503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0997   -3.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8083   -3.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8131   -4.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5975   -4.8912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0775   -4.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5897   -3.5593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0972   -2.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0894   -1.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6854   -5.0493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9780   -4.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9832   -3.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766   -3.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5676   -3.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5696   -4.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2768   -5.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -3.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593   -2.5967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522   -3.8229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443   -3.4147    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
 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  2  0
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756141

   ---

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: 1.44

#Rotatable Bonds: 3

Polar Surface Area: 95.59

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.60

CX Basic pKa: 2.15

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: -1.24

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