2-[(4-Isopropyl-cyclohexanecarbonyl)-amino]-3-phenyl-propionic acid

ID: ALA783

Chembl Id: CHEMBL783

Max Phase: Approved

First Approval: 2000

Molecular Formula: C19H27NO3

Molecular Weight: 317.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: D-nateglinide | Nateglinide | Senaglinide | A-4166 | AY-4166 | AY4166 | DJN 608 | DJN-608 | NSC-758695 | SDZ DJN 608 | SDZ-DJN-608

Trade Names(3): Nateglinide | Starlix | Starsis

Canonical SMILES:  CC(C)[C@H]1CC[C@H](C(=O)N[C@H](Cc2ccccc2)C(=O)O)CC1

Standard InChI:  InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1

Standard InChI Key:  OELFLUMRDSZNSF-BRWVUGGUSA-N

Alternative Forms

1. Parent:

   

   ALA783

   NATEGLINIDE

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 317.43

Molecular Weight (Monoisotopic): 317.1991

AlogP: 3.26

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.00

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 0.87

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: -0.23

References

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

20. Kaur J, Bhardwaj A, Huang Z, Narang D, Chen TY, Plane F, Knaus EE..  (2012)  Synthesis and biological investigations of nitric oxide releasing nateglinide and meglitinide type II antidiabetic prodrugs: in-vivo antihyperglycemic activities and blood pressure lowering studies.,  55  (17): [PMID:22916833] [10.1021/jm300997w]

21. Maddi S, Yamsani SK, Devandla A, Scriba G, Yamsani MR.  (2013)  Evidence of stereoselective and segmental-dependant transport of chiral antidiabetic drug nateglinide along the rat small intestine: possible role of efflux transporters,  22  (5): [10.1007/s00044-012-0234-4]

22. Maddi S, Yamsani SK, Devandla A, Scriba G, Yamsani MR.  (2013)  Evidence of stereoselective and segmental-dependant transport of chiral antidiabetic drug nateglinide along the rat small intestine: possible role of efflux transporters,  22  (5): [10.1007/s00044-012-0234-4]

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32. Unpublished dataset, 

33. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

34. 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]

35. 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]

36. 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]

37. 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]

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39. European Medicines Agency, 

Source

Source(13):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• TP-search Transporter Database
• CO-ADD antimicrobial screening data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• European Medicines Agency