3-(3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)-2-cyanoacrylamide

ID: ALA5278864

Max Phase: Preclinical

Molecular Formula: C16H11N5O

Molecular Weight: 289.30

Names and Identifiers

Canonical SMILES:  N#C/C(=C/c1cccc(-c2ncnc3[nH]ccc23)c1)C(N)=O

Standard InChI:  InChI=1S/C16H11N5O/c17-8-12(15(18)22)7-10-2-1-3-11(6-10)14-13-4-5-19-16(13)21-9-20-14/h1-7,9H,(H2,18,22)(H,19,20,21)/b12-7-

Standard InChI Key:  PBACTZXZNFJQGT-GHXNOFRVSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.3464   -4.2537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452   -5.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0580   -5.4904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -3.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7696   -4.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -5.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5580   -5.3346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0450   -4.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576   -3.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509   -3.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7637   -2.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7616   -1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0475   -1.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3339   -1.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394   -2.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731   -1.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866   -1.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8980   -1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6096   -0.9622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -2.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772   -3.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021   -3.0161    0.0000 N   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
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  4 10  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  3  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278864

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 289.30

Molecular Weight (Monoisotopic): 289.0964

AlogP: 2.02

#Rotatable Bonds: 3

Polar Surface Area: 108.45

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.87

CX Basic pKa: 4.63

CX LogP: 1.72

CX LogD: 1.72

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -0.77

References

1. Petri L, Egyed A, Bajusz D, Imre T, Hetényi A, Martinek T, Ábrányi-Balogh P, Keserű GM..  (2020)  An electrophilic warhead library for mapping the reactivity and accessibility of tractable cysteines in protein kinases.,  207  [PMID:32971426] [10.1016/j.ejmech.2020.112836]

Source

Source(1):

• Scientific Literature