ID: ALA17045

Max Phase: Phase

Molecular Formula: C24H31N5O2

Molecular Weight: 421.55

Molecule Type: Small molecule

Representations

Synonyms (3): Otenzepad | AF-DX 116 | AF-DX-116
Synonyms from Alternative Forms(3):

Canonical SMILES:  CCN(CC)CC1CCCCN1CC(=O)N1c2ccccc2C(=O)Nc2cccnc21

Standard InChI:  InChI=1S/C24H31N5O2/c1-3-27(4-2)16-18-10-7-8-15-28(18)17-22(30)29-21-13-6-5-11-19(21)24(31)26-20-12-9-14-25-23(20)29/h5-6,9,11-14,18H,3-4,7-8,10,15-17H2,1-2H3,(H,26,31)

Standard InChI Key:  UBRKDAVQCKZSPO-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 421.55

Molecular Weight (Monoisotopic): 421.2478

AlogP: 3.51

#Rotatable Bonds: 6

Polar Surface Area: 68.78

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.22

CX LogP: 2.76

CX LogD: 0.94

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.77

Np Likeness Score: -0.93

References

1. Messer WS, Ellerbrock BR, Smith DA, Hoss W..  (1989)  Regional differences in the binding of selective muscarinic receptor antagonists in rat brain: comparison with minimum-energy conformations.,  32  (6): [PMID:2724292] [10.1021/jm00126a004]

2. Cohen VI, Baumgold J, Jin B, De La Cruz R, Rzeszotarski WJ, Reba RC..  (1993)  Synthesis and structure-activity relationship of some 5-[[[(dialkylamino)alkyl]-1-piperidinyl]acetyl]-10,11-dihydro-5H- benzo[b,e][1,4]diazepin-11-ones as M2-selective antimuscarinics.,  36  (1): [PMID:8421282] [10.1021/jm00053a021]

3. Engel WW, Eberlein WG, Mihm G, Hammer R, Trummlitz G..  (1989)  Tricyclic compounds as selective muscarinic receptor antagonists. 3. Structure-selectivity relationships in a series of cardioselective (M2) antimuscarinics.,  32  (8): [PMID:2754696] [10.1021/jm00128a008]

4. Engel WW, Eberlein WG, Mihm G, Hammer R, Trummlitz G..  (1989)  Tricyclic compounds as selective muscarinic receptor antagonists. 3. Structure-selectivity relationships in a series of cardioselective (M2) antimuscarinics.,  32  (8): [PMID:2754696] [10.1021/jm00128a008]

5. Engel WW, Eberlein WG, Mihm G, Hammer R, Trummlitz G..  (1989)  Tricyclic compounds as selective muscarinic receptor antagonists. 3. Structure-selectivity relationships in a series of cardioselective (M2) antimuscarinics.,  32  (8): [PMID:2754696] [10.1021/jm00128a008]

6. Nilsson BM, Vargas HM, Hacksell U..  (1992)  Amide, urea, and carbamate analogues of the muscarinic agent [4-[[N-(3-chlorophenyl)carbamoyl]oxy]-2-butynyl]trimethylammonium chloride.,  35  (15): [PMID:1379640] [10.1021/jm00093a011]

7. Burke BJ, Dunn WJ, Hopfinger AJ..  (1994)  Construction of a molecular shape analysis-three-dimensional quantitative structure-analysis relationship for an analog series of pyridobenzodiazepinone inhibitors of muscarinic 2 and 3 receptors.,  37  (22): [PMID:7966137] [10.1021/jm00048a014]

8. Burke BJ, Dunn WJ, Hopfinger AJ..  (1994)  Construction of a molecular shape analysis-three-dimensional quantitative structure-analysis relationship for an analog series of pyridobenzodiazepinone inhibitors of muscarinic 2 and 3 receptors.,  37  (22): [PMID:7966137] [10.1021/jm00048a014]

9. Burke BJ, Dunn WJ, Hopfinger AJ..  (1994)  Construction of a molecular shape analysis-three-dimensional quantitative structure-analysis relationship for an analog series of pyridobenzodiazepinone inhibitors of muscarinic 2 and 3 receptors.,  37  (22): [PMID:7966137] [10.1021/jm00048a014]

10. Murgolo NJ, Kozlowski J, Tice MA, Hollinger FP, Brown JE, Zhou G, Taylor LA, McQuade RD.  (1996)  The N4 nitrogen of pirenzepine is responsible for selective binding of the M1 subtype human muscarinic receptor,  6  (7): [10.1016/0960-894X(96)00107-2]

11. PubChem BioAssay data set, 

12. PubChem BioAssay data set, 

13. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

14. Honda H, Tomizawa M, Casida JE..  (2007)  Insect muscarinic acetylcholine receptor: pharmacological and toxicological profiles of antagonists and agonists.,  55  (6): [PMID:17319687] [10.1021/jf0631934]

15. Zheng G, Smith AM, Huang X, Subramanian KL, Siripurapu KB, Deaciuc A, Zhan CG, Dwoskin LP..  (2013)  Structural modifications to tetrahydropyridine-3-carboxylate esters en route to the discovery of M5-preferring muscarinic receptor orthosteric antagonists.,  56  (4): [PMID:23379472] [10.1021/jm301774u]

16. PubChem BioAssay data set, 

17. 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]

18. 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]

19. 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]

20. 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]

21. 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]

22. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

23. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

24. 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]

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• CO-ADD antimicrobial screening data
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6