N-(3-((5-iodo-4-((3-(thiophene-2-carboxamido)propyl)amino)pyrimidin-2-yl)amino)phenyl)pyrrolidine-1-carboxamide

ID: ALA577784

Cas Number: 702675-74-9

PubChem CID: 10077147

Product Number: B126947, Order Now?

Max Phase: Preclinical

Molecular Formula: C23H26IN7O2S

Molecular Weight: 591.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BX-795 | 702675-74-9|BX795|BX-795|BX 795|N-[3-[[5-IODO-4-[[3-[(2-THIENYLCARBONYL)AMINO]PROPYL]AMINO]-2-PYRIMIDINYL]AMINO]PHENYL]-1-PYRROLIDINECARBOXAMIDE|N-(3-((5-iodo-4-((3-(thiophene-2-carboxamido)propyl)amino)pyrimidin-2-yl)amino)phenyl)pyrrolidine-1-carboxamide|N-[3-[[5-iodo-4-[3-(thiophene-2-carbonylamino)propylamino]pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxamide|N-{3-[(5-iodo-4-{[3-(thiophen-2-ylformamido)propyl]amino}pyrimidin-2-yl)amino]phenyl}pyrrolidine-1-carboxamide|BX-795 hydrShow More⌵

Canonical SMILES:  O=C(NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1I)c1cccs1

Standard InChI:  InChI=1S/C23H26IN7O2S/c24-18-15-27-22(30-20(18)25-9-5-10-26-21(32)19-8-4-13-34-19)28-16-6-3-7-17(14-16)29-23(33)31-11-1-2-12-31/h3-4,6-8,13-15H,1-2,5,9-12H2,(H,26,32)(H,29,33)(H2,25,27,28,30)

Standard InChI Key:  VAVXGGRQQJZYBL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    0.4319    0.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4307   -0.2065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8620   -0.2060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591    0.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    1.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5708    1.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997    1.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7169    0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4287    1.0605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1458    0.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8576    1.0699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120   -1.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5367   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7969   -0.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1620   -1.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8708   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676   -2.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5756   -3.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2858   -2.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -2.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751   -1.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4025   -0.6098    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9970   -1.7580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7126   -2.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634   -1.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083   -2.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387   -3.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2892   -4.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1136   -4.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699   -3.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    1.8586    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 16 17  1  0
 17 14  2  0
  3 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
 11 12  1  0
  6  1  1  0
 23 26  1  0
 12 13  2  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 12 14  1  0
 27 29  1  0
 30 31  1  0
 25 15  1  0
  5  7  1  0
  3  4  2  0
  7  8  1  0
 29 30  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
 14 25  1  0
  6 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA577784

   BX-795

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: 591.48

Molecular Weight (Monoisotopic): 591.0913

AlogP: 4.75

#Rotatable Bonds: 9

Polar Surface Area: 111.28

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.85

CX Basic pKa: 3.68

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: -2.12

References

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2. Okuzumi T, Fiedler D, Zhang C, Gray DC, Aizenstein B, Hoffman R, Shokat KM..  (2009)  Inhibitor hijacking of Akt activation.,  5  (7): [PMID:19465931] [10.1038/nchembio.183]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Genomics of Drug Sensitity in Cancer screening data, Wellcome Trust Sanger Institute,  [10.6019/CHEMBL1201861]

6. Lazarus MB, Shokat KM..  (2015)  Discovery and structure of a new inhibitor scaffold of the autophagy initiating kinase ULK1.,  23  (17): [PMID:26275681] [10.1016/j.bmc.2015.07.034]

7. Hall J, Brault A, Vincent F, Weng S, Wang H, Dumlao D, Aulabaugh A, Aivazian D, Castro D, Chen M, Culp J, Dower K, Gardner J, Hawrylik S, Golenbock D, Hepworth D, Horn M, Jones L, Jones P, Latz E, Li J, Lin LL, Lin W, Lin D, Lovering F, Niljanskul N, Nistler R, Pierce B, Plotnikova O, Schmitt D, Shanker S, Smith J, Snyder W, Subashi T, Trujillo J, Tyminski E, Wang G, Wong J, Lefker B, Dakin L, Leach K..  (2017)  Discovery of PF-06928215 as a high affinity inhibitor of cGAS enabled by a novel fluorescence polarization assay.,  12  (9): [PMID:28934246] [10.1371/journal.pone.0184843]

8. 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]

9. Thomson DW, Poeckel D, Zinn N, Rau C, Strohmer K, Wagner AJ, Graves AP, Perrin J, Bantscheff M, Duempelfeld B, Kasparcova V, Ramanjulu JM, Pesiridis GS, Muelbaier M, Bergamini G..  (2019)  Discovery of GSK8612, a Highly Selective and Potent TBK1 Inhibitor.,  10  (5): [PMID:31097999] [10.1021/acsmedchemlett.9b00027]

10. Sintim HO, Mikek CG, Wang M, Sooreshjani MA..  (2019)  Interrupting cyclic dinucleotide-cGAS-STING axis with small molecules.,  10  (12): [PMID:32206239] [10.1039/C8MD00555A]

11. Lefranc J, Schulze VK, Hillig RC, Briem H, Prinz F, Mengel A, Heinrich T, Balint J, Rengachari S, Irlbacher H, Stöckigt D, Bömer U, Bader B, Gradl SN, Nising CF, von Nussbaum F, Mumberg D, Panne D, Wengner AM..  (2020)  Discovery of BAY-985, a Highly Selective TBK1/IKKε Inhibitor.,  63  (2): [PMID:31859507] [10.1021/acs.jmedchem.9b01460]

12. 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]

13. 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]

14. 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]

15. 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]

16. 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]

17. Faisal M, Kim JH, Yoo KH, Roh EJ, Hong SS, Lee SH..  (2021)  Development and Therapeutic Potential of NUAKs Inhibitors.,  64  (1.0): [PMID:33356242] [10.1021/acs.jmedchem.0c00533]

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Source

Source(6):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset