RGB-286638

ID: ALA3545083

Cas Number: 784210-88-4

PubChem CID: 11285002

Product Number: R613171, Order Now?

Max Phase: Phase

Molecular Formula: C29H35N7O4

Molecular Weight: 545.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rgb-286638 | RGB 286638 | RGB-286638 free base|784210-88-4|RGB-286638|RGB286638|1-[3-[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]phenyl]-4-oxo-1H-indeno[1,2-c]pyrazol-5-yl]-3-morpholin-4-ylurea|784210-88-4 (free base)|1GAJ98SC2X|Urea, N-(1,4-dihydro-3-(4-((4-(2-methoxyethyl)-1-piperazinyl)methyl)phenyl)-4-oxoindeno(1,2-c)pyrazol-5-yl)-n'-4-morpholinyl-|UNII-1GAJ98SC2X|RGB 286638 free base|GTPL7744|CHEMBL3545083|SCHEMBL10087436|DTXSID00229072|EX-A557|BCP14399|BDBM50193093|HY-15504A|MFCD18633230|Show More⌵

Canonical SMILES:  COCCN1CCN(Cc2ccc(-c3n[nH]c4c3C(=O)c3c(NC(=O)NN5CCOCC5)cccc3-4)cc2)CC1

Standard InChI:  InChI=1S/C29H35N7O4/c1-39-16-13-34-9-11-35(12-10-34)19-20-5-7-21(8-6-20)26-25-27(32-31-26)22-3-2-4-23(24(22)28(25)37)30-29(38)33-36-14-17-40-18-15-36/h2-8H,9-19H2,1H3,(H,31,32)(H2,30,33,38)

Standard InChI Key:  XLSYZSRXVVCHLS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   -1.2591   -3.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111   -2.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712   -2.1406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793   -1.9744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475   -1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954   -1.6420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353   -2.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272   -2.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970   -3.0897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -3.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1909   -4.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692   -5.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773   -5.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -4.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -4.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -4.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -4.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055   -3.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266   -3.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071   -2.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7666   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2471   -1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0681   -1.4229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4086   -2.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2297   -2.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7102   -1.5846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5312   -1.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8717   -2.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6928   -2.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0333   -3.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3697   -0.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5486   -0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455   -1.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4650   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851   -4.8075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9209   -5.2968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -4.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8294   -3.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240   -2.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2 10  1  0
  3  4  1  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10 11  1  0
 11 12  2  0
 11 38  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 38  2  0
 16 17  2  0
 16 37  1  0
 17 18  1  0
 17 39  1  0
 18 19  1  0
 18 36  2  0
 19 20  2  0
 19 35  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 34  1  0
 23 24  1  0
 24 25  1  0
 24 33  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 32 33  1  0
 34 35  2  0
 36 37  1  0
 38 39  1  0
 39 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3545083

   RGB-286638

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 545.64

Molecular Weight (Monoisotopic): 545.2751

AlogP: 2.42

#Rotatable Bonds: 8

Polar Surface Area: 115.06

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.36

CX Basic pKa: 7.56

CX LogP: 2.14

CX LogD: 1.87

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.31

Np Likeness Score: -1.32

References

1. Unpublished dataset, 

2. Sonawane YA, Taylor MA, Napoleon JV, Rana S, Contreras JI, Natarajan A..  (2016)  Cyclin Dependent Kinase 9 Inhibitors for Cancer Therapy.,  59  (19): [PMID:27171036] [10.1021/acs.jmedchem.6b00150]

3. Klaeger S, Heinzlmeir S and Wilhelm M et al.  (2017)  The target landscape of clinical kinase drugs.,  358  (6367): [PMID:29191878] [10.1126/science.aan4368]

4. 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]

5. 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]

6. 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]

7. 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]

8. 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]

9. 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]

10. Xie Z, Hou S, Yang X, Duan Y, Han J, Wang Q, Liao C..  (2022)  Lessons Learned from Past Cyclin-Dependent Kinase Drug Discovery Efforts.,  65  (9.0): [PMID:35235745] [10.1021/acs.jmedchem.1c02190]

11. Huang Z, Wang T, Wang C, Fan Y..  (2022)  CDK9 inhibitors in cancer research.,  13  (6.0): [PMID:35814933] [10.1039/d2md00040g]

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

Source

Source(6):

• Scientific Literature
• Clinical Candidates
• Kuster lab chemical proteomics drug profiling
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset