1-(4-(4-(2-(isopropylsulfonyl)phenylamino)-1H-pyrrolo[2,3-b]pyridin-6-ylamino)-3-methoxyphenyl)piperidin-4-ol

ID: ALA1235786

Cas Number: 1125593-20-5

PubChem CID: 25195352

Product Number: M612011, Order Now?

Max Phase: Preclinical

Molecular Formula: C28H33N5O4S

Molecular Weight: 535.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N2CCC(O)CC2)ccc1Nc1cc(Nc2ccccc2S(=O)(=O)C(C)C)c2cc[nH]c2n1

Standard InChI:  InChI=1S/C28H33N5O4S/c1-18(2)38(35,36)26-7-5-4-6-23(26)30-24-17-27(32-28-21(24)10-13-29-28)31-22-9-8-19(16-25(22)37-3)33-14-11-20(34)12-15-33/h4-10,13,16-18,20,34H,11-12,14-15H2,1-3H3,(H3,29,30,31,32)

Standard InChI Key:  NMJMRSQTDLRCRQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
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    0.1184    4.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329    5.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329    6.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474    4.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474    4.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329    3.7301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329    2.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474    2.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474    1.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2619    1.2551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2619    0.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184    2.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184    1.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329    1.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329    0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184    0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960    0.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0951    0.2725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105   -0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960   -1.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960   -2.0449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -2.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329   -2.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474   -2.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5474   -3.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8329   -3.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -3.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960   -3.6949    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -2.9804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1835   -4.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105   -4.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105   -4.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250   -3.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  7  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  0
  8  9  2  0
 13  8  1  0
  9 10  1  0
 10 11  1  0
 15 10  2  0
 12 11  1  0
 14 13  2  0
 15 14  1  0
 15 16  1  0
 17 16  1  0
 17 18  2  0
 17 19  1  0
 18 25  1  0
 20 19  2  0
 20 21  1  0
 24 20  1  0
 22 21  1  0
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 24 23  1  0
 25 24  2  0
 25 26  1  0
 27 26  1  0
 27 28  2  0
 27 32  1  0
 29 28  1  0
 30 29  2  0
 31 30  1  0
 32 31  2  0
 32 33  1  0
 34 33  2  0
 35 33  2  0
 36 33  1  0
 36 37  1  0
 36 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1235786

   MPS1-IN-1

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: 535.67

Molecular Weight (Monoisotopic): 535.2253

AlogP: 5.20

#Rotatable Bonds: 8

Polar Surface Area: 119.58

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.21

CX LogP: 3.88

CX LogD: 3.67

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: -1.03

References

1. Sugimoto Y, Sawant DB, Fisk HA, Mao L, Li C, Chettiar S, Li PK, Darby MV, Brueggemeier RW..  (2017)  Novel pyrrolopyrimidines as Mps1/TTK kinase inhibitors for breast cancer.,  25  (7): [PMID:28259529] [10.1016/j.bmc.2017.02.030]

2. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

3. 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]

4. 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]

5. 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]

6. 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]

7.  (2021)  EUbOPEN Chemogenomics Library wave 1,  [10.6019/CHEMBL4689842]

8. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

9. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

10. EUbOPEN.  (2023)  Affinity Phenotypic Cellular Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5209897]

11. EUbOPEN.  (2023)  Affinity Biochemical Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5210307]

12. EUbOPEN.  (2023)  Selectivity Literature for EUbOPEN Chemogenomics Library wave 3,  [10.6019/CHEMBL5212743]

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

Source

Source(6):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• EUbOPEN Chemogenomic Library
• Fraunhofer HDAC6
• Literature data from EUbOPEN Chemogenomic Library
• EU-OPENSCREEN dataset