ID: ALA371197

Max Phase: Unknown

Molecular Formula: C8H15NO3

Molecular Weight: 173.21

Molecule Type: Small molecule

Representations

Synonyms (1): Swainsonine
Synonyms from Alternative Forms(1):

Canonical SMILES:  O[C@H]1[C@H]2[C@H](O)CCCN2C[C@H]1O

Standard InChI:  InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1

Standard InChI Key:  FXUAIOOAOAVCGD-WCTZXXKLSA-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: 173.21

Molecular Weight (Monoisotopic): 173.1052

AlogP: -1.45

#Rotatable Bonds: 0

Polar Surface Area: 63.93

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.28

CX Basic pKa: 9.47

CX LogP: -1.41

CX LogD: -3.47

Aromatic Rings: 0

Heavy Atoms: 12

QED Weighted: 0.42

Np Likeness Score: 1.57

References

1. Winkler DA, Holan G..  (1989)  Design of potential anti-HIV agents. 1. Mannosidase inhibitors.,  32  (9): [PMID:2504921] [10.1021/jm00129a011]

2. Fiaux H, Popowycz F, Favre S, Schütz C, Vogel P, Gerber-Lemaire S, Juillerat-Jeanneret L..  (2005)  Functionalized pyrrolidines inhibit alpha-mannosidase activity and growth of human glioblastoma and melanoma cells.,  48  (13): [PMID:15974577] [10.1021/jm0409019]

3. Chen IJ, Chen HL, Demetriou M..  (2007)  Lateral compartmentalization of T cell receptor versus CD45 by galectin-N-glycan binding and microfilaments coordinate basal and activation signaling.,  282  (48): [PMID:17897956] [10.1074/jbc.m706923200]

4. Fiaux H, Kuntz DA, Hoffman D, Janzer RC, Gerber-Lemaire S, Rose DR, Juillerat-Jeanneret L..  (2008)  Functionalized pyrrolidine inhibitors of human type II alpha-mannosidases as anti-cancer agents: optimizing the fit to the active site.,  16  (15): [PMID:18599296] [10.1016/j.bmc.2008.06.021]

5. Molyneux RJ, McKenzie RA, O'Sullivan BM, Elbein AD..  (1995)  Identification of the glycosidase inhibitors swainsonine and calystegine B2 in Weir vine (Ipomoea sp. Q6 [aff. calobra]) and correlation with toxicity.,  58  (6): [PMID:7673932] [10.1021/np50120a009]

6. Molyneux RJ, Pan YT, Tropea JE, Elbein AD, Lawyer CH, Hughes DJ, Fleet GW..  (1993)  2-Hydroxymethyl-3,4-dihydroxy-6-methyl-pyrrolidine (6-deoxy-DMDP), an alkaloid beta-mannosidase inhibitor from seeds of Angylocalyx pynaertii.,  56  (8): [PMID:8229017] [10.1021/np50098a020]

7. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

8. Zhu Y, Suits MD, Thompson AJ, Chavan S, Dinev Z, Dumon C, Smith N, Moremen KW, Xiang Y, Siriwardena A, Williams SJ, Gilbert HJ, Davies GJ..  (2010)  Mechanistic insights into a Ca2+-dependent family of alpha-mannosidases in a human gut symbiont.,  6  (2): [PMID:20081828] [10.1038/nchembio.278]

9. Poláková M, Šesták S, Lattová E, Petruš L, Mucha J, Tvaroška I, Kóňa J..  (2011)  α-D-mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II.,  46  (3): [PMID:21295890] [10.1016/j.ejmech.2011.01.012]

10. PubChem BioAssay data set, 

11. Mane RS, Ghosh S, Singh S, Chopade BA, Dhavale DD..  (2011)  Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors.,  19  (22): [PMID:22001328] [10.1016/j.bmc.2011.09.046]

12. PubChem BioAssay data set, 

13. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

14. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

15. PubChem BioAssay data set, 

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. 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]

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]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6