3-(6-ethynyl-9H-purin-2-ylamino)-N,N-dimethylbenzamide

ID: ALA4775990

PubChem CID: 162643411

Max Phase: Preclinical

Molecular Formula: C16H14N6O

Molecular Weight: 306.33

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H14N6O/c1-4-12-13-14(18-9-17-13)21-16(20-12)19-11-7-5-6-10(8-11)15(23)22(2)3/h1,5-9H,2-3H3,(H2,17,18,19,20,21)

Standard InChI Key:  SMNPXRSXMMRVQE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   33.6107  -12.0061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6096  -12.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3176  -13.2346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3158  -11.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0245  -12.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0293  -12.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8137  -13.0755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2937  -12.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8059  -11.7436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3134  -10.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3055   -9.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9016  -13.2336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1942  -12.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1994  -12.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4928  -11.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7838  -12.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7858  -12.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4929  -13.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0792  -13.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3704  -12.8317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0814  -14.0556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3681  -12.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6638  -13.2423    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
 17 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4775990

   ---

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: 306.33

Molecular Weight (Monoisotopic): 306.1229

AlogP: 1.78

#Rotatable Bonds: 3

Polar Surface Area: 86.80

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.60

CX Basic pKa: 2.19

CX LogP: 1.66

CX LogD: 1.65

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.72

Np Likeness Score: -1.63

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