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

ID: ALA4099596

PubChem CID: 137661645

Max Phase: Preclinical

Molecular Formula: C13H11N7O2S

Molecular Weight: 329.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c[nH]c2nc(N)nc(Nc3ccc(S(N)(=O)=O)cc3)c12

Standard InChI:  InChI=1S/C13H11N7O2S/c14-5-7-6-17-11-10(7)12(20-13(15)19-11)18-8-1-3-9(4-2-8)23(16,21)22/h1-4,6H,(H2,16,21,22)(H4,15,17,18,19,20)

Standard InChI Key:  XRUSSNUKOCIDFS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   17.1486  -15.2460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5614  -15.9559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.9698  -15.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6937  -18.8077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6926  -19.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4006  -20.0362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3988  -18.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1074  -18.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1122  -19.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8923  -19.8712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3696  -19.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8845  -18.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9845  -20.0353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1314  -17.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3794  -16.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3964  -17.5817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6875  -17.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6884  -16.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9803  -15.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2728  -16.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2779  -17.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9865  -17.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8574  -16.3692    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
  7 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20  2  1  0
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099596

   ---

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: 329.35

Molecular Weight (Monoisotopic): 329.0695

AlogP: 0.80

#Rotatable Bonds: 3

Polar Surface Area: 163.57

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.55

CX Basic pKa: 5.46

CX LogP: 0.86

CX LogD: 0.86

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: -1.47

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