3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine

ID: ALA2147777

Cas Number: 760937-92-6

PubChem CID: 11949652

Product Number: T127809, Order Now?

Max Phase: Approved

First Approval: 2012

Molecular Formula: C22H30N6OS

Molecular Weight: 426.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Teneligliptin | MP-513 | Teneligliptin|760937-92-6|Teneligliptin [INN]|MP-513|Teliglietin|[(2S,4S)-4-[4-(5-methyl-2-phenylpyrazol-3-yl)piperazin-1-yl]pyrrolidin-2-yl]-(1,3-thiazolidin-3-yl)methanone|28ZHI4CF9C|CHEMBL2147777|Teneligliptin (INN)|906093-29-6|{(2s,4s)-4-[4-(3-Methyl-1-Phenyl-1h-Pyrazol-5-Yl)piperazin-1-Yl]pyrrolidin-2-Yl}(1,3-Thiazolidin-3-Yl)methanone|UNII-28ZHI4CF9C|Teneli|((2S,4S)-4-(4-(3-METHYL-1-PHENYL-1H-PYRAZOL-5-YL)PIPERAZIN-1-YL)PYRROLIDIN-2-YL)(1,3-THIAZOLIDIN-3-YL)METHANOShow More⌵

Canonical SMILES:  Cc1cc(N2CCN([C@@H]3CN[C@H](C(=O)N4CCSC4)C3)CC2)n(-c2ccccc2)n1

Standard InChI:  InChI=1S/C22H30N6OS/c1-17-13-21(28(24-17)18-5-3-2-4-6-18)26-9-7-25(8-10-26)19-14-20(23-15-19)22(29)27-11-12-30-16-27/h2-6,13,19-20,23H,7-12,14-16H2,1H3/t19-,20-/m0/s1

Standard InChI Key:  WGRQANOPCQRCME-PMACEKPBSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   13.9480  -20.5803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5327  -21.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9411  -22.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7665  -22.0119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1817  -21.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7717  -20.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2510  -22.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9927  -23.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6580  -23.9570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3266  -23.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0759  -22.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0322  -23.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0147  -24.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7013  -23.4196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4837  -23.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9705  -23.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4875  -22.3407    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7022  -22.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724  -19.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7340  -19.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0733  -18.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3992  -19.1084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6435  -19.8963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2227  -20.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3967  -20.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9724  -21.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3729  -22.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2021  -22.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6227  -21.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0847  -17.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  1  2  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
  1  6  1  0
  1 19  1  0
 19 20  2  0
  2  3  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
 11  7  1  0
  7  4  1  1
 24 25  2  0
  3  4  1  0
 25 26  1  0
 10 12  1  1
 26 27  2  0
  4  5  1  0
 27 28  1  0
 12 13  2  0
 28 29  2  0
 29 24  1  0
 23 24  1  0
  5  6  1  0
 21 30  1  0
 12 14  1  0
 14 15  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA2147777

   [(2S,4S)-4-[4-(5-methyl-2-phenylpyrazol-3-yl)piperazin-1-yl]pyrrolidin-2-yl]-(1,3-thiazolidin-3-yl)methanone;hydrobromide

2. Parent:

   

   ALA2147777

   Teneligliptin

Molecule Features

Natural Product: No

Oral: Yes

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: 426.59

Molecular Weight (Monoisotopic): 426.2202

AlogP: 1.57

#Rotatable Bonds: 4

Polar Surface Area: 56.64

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.38

CX LogP: 1.42

CX LogD: -0.54

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.80

Np Likeness Score: -1.42

References

1. Yoshida T, Akahoshi F, Sakashita H, Kitajima H, Nakamura M, Sonda S, Takeuchi M, Tanaka Y, Ueda N, Sekiguchi S, Ishige T, Shima K, Nabeno M, Abe Y, Anabuki J, Soejima A, Yoshida K, Takashina Y, Ishii S, Kiuchi S, Fukuda S, Tsutsumiuchi R, Kosaka K, Murozono T, Nakamaru Y, Utsumi H, Masutomi N, Kishida H, Miyaguchi I, Hayashi Y..  (2012)  Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine): a highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes.,  20  (19): [PMID:22959556] [10.1016/j.bmc.2012.08.012]

2. Li N, Wang LJ, Jiang B, Li XQ, Guo CL, Guo SJ, Shi DY..  (2018)  Recent progress of the development of dipeptidyl peptidase-4 inhibitors for the treatment of type 2 diabetes mellitus.,  151  [PMID:29609120] [10.1016/j.ejmech.2018.03.041]

3. Unpublished dataset, 

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. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

6. Schnapp G, Klein T, Hoevels Y, Bakker RA, Nar H..  (2016)  Comparative Analysis of Binding Kinetics and Thermodynamics of Dipeptidyl Peptidase-4 Inhibitors and Their Relationship to Structure.,  59  (16): [PMID:27438064] [10.1021/acs.jmedchem.6b00475]

7. 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]

8. 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]

9. 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]

10. 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]

11. WHO Anatomical Therapeutic Chemical Classification, 

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

13. 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]

14. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(6):

• Scientific Literature
• Clinical Candidates
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6