2-Amino-4-(4-(2-hydroxyethyl)piperazin-1-yl)-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

ID: ALA4102550

PubChem CID: 137657569

Max Phase: Preclinical

Molecular Formula: C13H17N7O

Molecular Weight: 287.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c[nH]c2nc(N)nc(N3CCN(CCO)CC3)c12

Standard InChI:  InChI=1S/C13H17N7O/c14-7-9-8-16-11-10(9)12(18-13(15)17-11)20-3-1-19(2-4-20)5-6-21/h8,21H,1-6H2,(H3,15,16,17,18)

Standard InChI Key:  UVKWLMKUGNQKSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   12.7847  -20.9745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7836  -21.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4916  -22.2030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4898  -20.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1985  -20.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2033  -21.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9833  -22.0380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4607  -21.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9755  -20.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0756  -22.2021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2224  -19.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4704  -19.1585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4874  -19.7485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1919  -19.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1914  -18.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4843  -18.1168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7760  -18.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7748  -19.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4849  -17.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1930  -16.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1936  -16.0744    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
  2 10  1  0
 11 12  3  0
  9 11  1  0
  4 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102550

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 287.33

Molecular Weight (Monoisotopic): 287.1495

AlogP: -0.47

#Rotatable Bonds: 3

Polar Surface Area: 118.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.04

CX Basic pKa: 7.36

CX LogP: 0.08

CX LogD: -0.28

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.70

Np Likeness Score: -1.29

References

1. Anthony NG, Baiget J, Berretta G, Boyd M, Breen D, Edwards J, Gamble C, Gray AI, Harvey AL, Hatziieremia S, Ho KH, Huggan JK, Lang S, Llona-Minguez S, Luo JL, McIntosh K, Paul A, Plevin RJ, Robertson MN, Scott R, Suckling CJ, Sutcliffe OB, Young LC, Mackay SP..  (2017)  Inhibitory Kappa B Kinase α (IKKα) Inhibitors That Recapitulate Their Selectivity in Cells against Isoform-Related Biomarkers.,  60  (16): [PMID:28737909] [10.1021/acs.jmedchem.7b00484]

Source

Source(1):

• Scientific Literature