2-(4-(6-((3S,5R)-3,5-dimethylpiperazin-1-yl)-4-methylpyridin-3-yl)phenyl)-7-methyl-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

ID: ALA4101890

PubChem CID: 135905416

Product Number: A422039, Order Now?

Max Phase: Preclinical

Molecular Formula: C25H28N6O

Molecular Weight: 428.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(N2C[C@@H](C)N[C@@H](C)C2)ncc1-c1ccc(-c2nc3c(ccn3C)c(=O)[nH]2)cc1

Standard InChI:  InChI=1S/C25H28N6O/c1-15-11-22(31-13-16(2)27-17(3)14-31)26-12-21(15)18-5-7-19(8-6-18)23-28-24-20(25(32)29-23)9-10-30(24)4/h5-12,16-17,27H,13-14H2,1-4H3,(H,28,29,32)/t16-,17+

Standard InChI Key:  WCPTUQOMNJBIET-CALCHBBNSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   23.2266  -10.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2255  -11.2366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9377  -11.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6514  -11.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6486  -10.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9359  -10.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3604  -11.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3604  -12.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0720  -12.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7842  -12.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7802  -11.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0680  -11.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5195  -10.0006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5213   -9.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8134   -8.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0993   -9.1752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0975   -9.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8099  -10.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4954  -12.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4959  -13.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2048  -14.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2040  -12.4569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9133  -12.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9139  -13.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6937  -13.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1767  -13.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6927  -12.6155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8163   -7.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3844  -10.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2052  -14.9228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9489  -11.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3589   -9.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  4  7  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
  1 13  1  0
 19 20  1  0
 19 22  2  0
 20 21  1  0
 21 24  1  0
 23 22  1  0
 10 19  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  1  0
 15 28  1  1
 17 29  1  1
 21 30  2  0
 27 31  1  0
  5 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101890

   AZ 6102

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

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: 428.54

Molecular Weight (Monoisotopic): 428.2325

AlogP: 3.49

#Rotatable Bonds: 3

Polar Surface Area: 78.84

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.84

CX Basic pKa: 9.00

CX LogP: 2.92

CX LogD: 2.57

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -0.79

References

1. Thorsell AG, Ekblad T, Karlberg T, Löw M, Pinto AF, Trésaugues L, Moche M, Cohen MS, Schüler H..  (2017)  Structural Basis for Potency and Promiscuity in Poly(ADP-ribose) Polymerase (PARP) and Tankyrase Inhibitors.,  60  (4): [PMID:28001384] [10.1021/acs.jmedchem.6b00990]

2. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

3. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

4. Liu Z, Wang P, Wold EA, Song Q, Zhao C, Wang C, Zhou J..  (2021)  Small-Molecule Inhibitors Targeting the Canonical WNT Signaling Pathway for the Treatment of Cancer.,  64  (8.0): [PMID:33822624] [10.1021/acs.jmedchem.0c01799]

5. Fraunhofer Institute for Translational Medicine and Pharmacology - Discovery Research – ScreeningPort.  (2021)  ECBD screening data for assay EOS300033,  [10.6019/EOS300033]

6. Institute for Molecular Medicine Finland - High Throughput Biomedicine Unit.  (2023)  ECBD screening data for assay EOS300108,  [10.6019/EOS300108]

Source

Source(3):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• EU-OPENSCREEN dataset