ID: ALA286494

Max Phase: Phase

Molecular Formula: C30H16O8

Molecular Weight: 504.45

Molecule Type: Small molecule

Representations

Synonyms (6): Hipericin | Hypericin | Hypericum red | NSC-407313 | SGX-301 | SGX301
Synonyms from Alternative Forms(6):

Canonical SMILES:  Cc1cc(O)c2c(=O)c3c(O)cc(O)c4c5c(O)cc(O)c6c(=O)c7c(O)cc(C)c8c1c2c(c34)c(c78)c65

Standard InChI:  InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3

Standard InChI Key:  BTXNYTINYBABQR-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: 504.45

Molecular Weight (Monoisotopic): 504.0845

AlogP: 5.08

#Rotatable Bonds: 0

Polar Surface Area: 155.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.65

CX Basic pKa: 3.37

CX LogP: 7.70

CX LogD: 6.41

Aromatic Rings: 8

Heavy Atoms: 38

QED Weighted: 0.12

Np Likeness Score: 0.61

References

1. Fehr M, Carpenter S, Petrich J.  (1994)  The role of oxygen in the photoinduced antiviral activity of hypericin,  4  (11): [10.1016/S0960-894X(01)80357-7]

2. Carlson HA, Masukawa KM, Rubins K, Bushman FD, Jorgensen WL, Lins RD, Briggs JM, McCammon JA..  (2000)  Developing a dynamic pharmacophore model for HIV-1 integrase.,  43  (11): [PMID:10841789] [10.1021/jm990322h]

3. Kraus GA, Zhang W, Carpenter S, Wannemuehler Y.  (1995)  The synthesis and biological evaluation of hypericin analogs,  5  (22): [10.1016/0960-894X(95)00458-6]

4. Müller K, Prinz H, Gawlik I, Ziereis K, Huang HS..  (1997)  Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity.,  40  (23): [PMID:9371243] [10.1021/jm970292n]

5. Sauviat MP, Colas A, Chauveau MJ, Drapier JC, Négrerie M..  (2007)  Hypericin activates L-type Ca2+ channels in cardiac myocytes.,  70  (4): [PMID:17291039] [10.1021/np060309h]

6. Coenye T, Honraet K, Rigole P, Nadal Jimenez P, Nelis HJ..  (2007)  In vitro inhibition of Streptococcus mutans biofilm formation on hydroxyapatite by subinhibitory concentrations of anthraquinones.,  51  (4): [PMID:17220400] [10.1128/aac.00999-06]

7. Kusari S, Lamshöft M, Zühlke S, Spiteller M..  (2008)  An endophytic fungus from Hypericum perforatum that produces hypericin.,  71  (2): [PMID:18220354] [10.1021/np070669k]

8. Kusari S, Zühlke S, Kosuth J, Cellárová E, Spiteller M..  (2009)  Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis.,  72  (10): [PMID:19746917] [10.1021/np9002977]

9. Nahrstedt A, Butterweck V..  (2010)  Lessons learned from herbal medicinal products: the example of St. John's Wort (perpendicular).,  73  (5): [PMID:20408551] [10.1021/np1000329]

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]

13. Sorrentino F, Karioti A, Gratteri P, Rigobello MP, Scutari G, Messori L, Bindoli A, Chioccioli M, Gabbiani C, Bergonzi MC, Bilia AR..  (2011)  Hypericins and thioredoxin reductase: Biochemical and docking studies disclose the molecular basis for effective inhibition by naphthodianthrones.,  19  (1): [PMID:21106380] [10.1016/j.bmc.2010.10.045]

14. PubChem BioAssay data set, 

15. PubChem BioAssay data set, 

16. PubChem BioAssay data set, 

17. 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]

18. Cleenewerck M, Grootaert MOJ, Gladysz R, Adriaenssens Y, Roelandt R, Joossens J, Lambeir AM, De Meyer GRY, Declercq W, Augustyns K, Martinet W, Van der Veken P..  (2016)  Inhibitor screening and enzymatic activity determination for autophagy target Atg4B using a gel electrophoresis-based assay.,  123  [PMID:27517808] [10.1016/j.ejmech.2016.07.073]

19. Niu W, Wu P, Chen F, Wang J, Shang X, Xu C..  (2017)  Discovery of selective cystathionine β-synthase inhibitors by high-throughput screening with a fluorescent thiol probe.,  8  (1): [PMID:30108705] [10.1039/C6MD00493H]

20. Unpublished dataset, 

21. 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]

22. 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]

23. 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]

24. 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]

25. 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]

26. Oliveri V.  (2019)  Toward the discovery and development of effective modulators of α-synuclein amyloid aggregation.,  167  [PMID:30743095] [10.1016/j.ejmech.2019.01.045]

27. Petrova ON,Lamarre I,Fasani F,Grillon C,Negrerie M.  (2020)  Soluble Guanylate Cyclase Inhibitors Discovered among Natural Compounds.,  83  (12.0): [PMID:33290062] [10.1021/acs.jnatprod.0c00854]

28. 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]

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

30. Zhang L, Zhang G, Xu S, Song Y..  (2021)  Recent advances of quinones as a privileged structure in drug discovery.,  223  [PMID:34153576] [10.1016/j.ejmech.2021.113632]

31. Yang G, Li Y, Zhao Y, Ouyang L, Chen Y, Liu B, Liu J..  (2021)  Targeting Atg4B for cancer therapy: Chemical mediators.,  209  [PMID:33077263] [10.1016/j.ejmech.2020.112917]

32. International Nonproprietary Names for Pharmaceutical Substances (INN), 

Source

Source(7):

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