ID: ALA344760

Max Phase: Phase

Molecular Formula: C3H4N2S

Molecular Weight: 100.15

Molecule Type: Small molecule

Representations

Synonyms (4): Aminothiazole | NSC-1900 | RP 2921 | RP-2921
Synonyms from Alternative Forms(4):

Canonical SMILES:  Nc1nccs1

Standard InChI:  InChI=1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)

Standard InChI Key:  RAIPHJJURHTUIC-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 100.15

Molecular Weight (Monoisotopic): 100.0095

AlogP: 0.73

#Rotatable Bonds: 0

Polar Surface Area: 38.91

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 5.09

CX LogP: 0.49

CX LogD: 0.49

Aromatic Rings: 1

Heavy Atoms: 6

QED Weighted: 0.52

Np Likeness Score: -1.79

References

1. Ríos-Santamarina I, García-Domenech R, Gálvez J, Cortijo J, Santamaria P, Morcillo E..  (1998)  New bronchodilators selected by molecular topology.,  8  (5): [PMID:9871602] [10.1016/s0960-894x(98)00056-0]

2. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

3. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

4. Castaño T, Encinas A, Pérez C, Castro A, Campillo NE, Gil C..  (2008)  Design, synthesis, and evaluation of potential inhibitors of nitric oxide synthase.,  16  (11): [PMID:18477512] [10.1016/j.bmc.2008.04.036]

5. Cao X, You QD, Li ZY, Guo QL, Shang J, Yan M, Chern JW, Chen ML..  (2008)  Design and synthesis of 7-alkoxy-4-heteroarylamino-3-quinolinecarbonitriles as dual inhibitors of c-Src kinase and nitric oxide synthase.,  16  (11): [PMID:18485715] [10.1016/j.bmc.2008.04.065]

6. Cao X, You QD, Li ZY, Liu XR, Xu D, Guo QL, Shang J, Chern JW, Chen ML..  (2008)  The design, synthesis and biological evaluation of 7-alkoxy-4-heteroarylamino-3-cyanoquinolines as dual inhibitors of c-Src and iNOS.,  18  (23): [PMID:18930653] [10.1016/j.bmcl.2008.10.006]

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

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

10. Meltzer-Mats E, Babai-Shani G, Pasternak L, Uritsky N, Getter T, Viskind O, Eckel J, Cerasi E, Senderowitz H, Sasson S, Gruzman A..  (2013)  Synthesis and mechanism of hypoglycemic activity of benzothiazole derivatives.,  56  (13): [PMID:23750537] [10.1021/jm4001488]

11. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

12. PubChem BioAssay data set, 

13. Waring MJ, Clarke DS, Fenwick MD, Godfrey L, Groombridge SD, Johnstone C, McKerrecher D, Pike KG, Rayner JW, Robb GR, Wilson I.  (2012)  Property based optimisation of glucokinase activators discovery of the phase IIb clinical candidate AZD1656,  3  (9): [10.1039/C2MD20077E]

14. PubChem BioAssay data set, 

15. Nong W, Zhao A, Wei J, Lin X, Wang L, Lin C..  (2017)  Synthesis and biological evaluation of a new series of cinnamic acid amide derivatives as potent haemostatic agents containing a 2-aminothiazole substructure.,  27  (18): [PMID:28844387] [10.1016/j.bmcl.2017.07.058]

16. 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]

17. 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]

18. 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]

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

20. 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]

21. Proj M, Hrast M, Knez D, Bozovičar K, Grabrijan K, Meden A, Gobec S, Frlan R..  (2022)  Fragment-Sized Thiazoles in Fragment-Based Drug Discovery Campaigns: Friend or Foe?,  13  (12.0): [PMID:36518695] [10.1021/acsmedchemlett.2c00429]

Source

Source(6):

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