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

ID: ALA4100931

PubChem CID: 137659346

Max Phase: Preclinical

Molecular Formula: C20H16N6O2S

Molecular Weight: 404.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NS(=O)(=O)c2ccc(-c3nc(N)nc4[nH]cc(C#N)c34)cc2)cc1

Standard InChI:  InChI=1S/C20H16N6O2S/c1-12-2-6-15(7-3-12)26-29(27,28)16-8-4-13(5-9-16)18-17-14(10-21)11-23-19(17)25-20(22)24-18/h2-9,11,26H,1H3,(H3,22,23,24,25)

Standard InChI Key:  GUBLWPFJYWDJRS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   25.2751  -19.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0676  -19.3278    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.8572  -18.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3769  -23.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3758  -23.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0838  -24.2336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0820  -22.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7906  -23.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7954  -23.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5755  -24.0686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0528  -23.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5677  -22.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6677  -24.2327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8146  -21.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0626  -21.1890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0768  -21.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7849  -21.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7828  -20.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0733  -20.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3645  -20.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3701  -21.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7757  -18.9193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7722  -18.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4799  -17.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4767  -16.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7667  -16.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0584  -16.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0651  -17.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7621  -15.6514    0.0000 C   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
 19  2  1  0
  2 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100931

   ---

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: 404.46

Molecular Weight (Monoisotopic): 404.1055

AlogP: 3.19

#Rotatable Bonds: 4

Polar Surface Area: 137.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.86

CX Basic pKa: 4.68

CX LogP: 3.26

CX LogD: 3.14

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.35

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