2-(2-Amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-benzenesulfonamide

ID: ALA4103966

PubChem CID: 137656635

Max Phase: Preclinical

Molecular Formula: C13H10N6O2S

Molecular Weight: 314.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c[nH]c2nc(N)nc(-c3ccccc3S(N)(=O)=O)c12

Standard InChI:  InChI=1S/C13H10N6O2S/c14-5-7-6-17-12-10(7)11(18-13(15)19-12)8-3-1-2-4-9(8)22(16,20)21/h1-4,6H,(H2,16,20,21)(H3,15,17,18,19)

Standard InChI Key:  BPVCLISCVQALND-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   19.2618  -11.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8573  -10.9495    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.4483  -11.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5699  -12.1670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5688  -12.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2768  -13.3955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2750  -11.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9836  -12.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9884  -12.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7685  -13.2305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2458  -12.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7607  -11.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8607  -13.3946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0076  -11.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2555  -10.3509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2698  -10.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9779  -10.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9758   -9.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2663   -9.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5575   -9.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5631  -10.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1477  -10.5483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  5 13  1  0
 14 15  3  0
 12 14  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  7 16  1  0
 21  2  1  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103966

   ---

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: 314.33

Molecular Weight (Monoisotopic): 314.0586

AlogP: 0.73

#Rotatable Bonds: 2

Polar Surface Area: 151.54

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: 3.90

CX LogP: 0.86

CX LogD: 0.86

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: -0.98

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