ID: ALA15891

Max Phase: Approved

First Approval: 1974

Molecular Formula: C6H6Cl6

Molecular Weight: 290.83

Molecule Type: Small molecule

Representations

Synonyms (12): Benzene hexachloride gamma | Benzene hexachloride, gamma | Gamma benzene hexachloride | gamma-Hexachlorocyclohexane | Gammahexachlorcyclohexane | Gammallin | Gammaxene | Hexachlorane | Hexicide | Lindane | Lindanum | NSC-755895
Synonyms from Alternative Forms(12):

Trade Names(10): Esoderm | Gamene | Gamma Benzene HCl | Gexane | Kwell | Lindane | Lorexane | Lorexane no 3 | Quellada | Scabene

Canonical SMILES:  Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl

Standard InChI:  InChI=1S/C6H6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-6H/t1-,2-,3-,4+,5+,6+

Standard InChI Key:  JLYXXMFPNIAWKQ-GNIYUCBRSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 290.83

Molecular Weight (Monoisotopic): 287.8601

AlogP: 3.64

#Rotatable Bonds: 0

Polar Surface Area: 0.00

Molecular Species:

HBA: 0

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 0

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.35

CX LogD: 4.35

Aromatic Rings: 0

Heavy Atoms: 12

QED Weighted: 0.60

Np Likeness Score: 0.18

References

1. Jorgensen WL, Duffy EM..  (2000)  Prediction of drug solubility from Monte Carlo simulations.,  10  (11): [PMID:10866370] [10.1016/s0960-894x(00)00172-4]

2. Andrews PR, Craik DJ, Martin JL..  (1984)  Functional group contributions to drug-receptor interactions.,  27  (12): [PMID:6094812] [10.1021/jm00378a021]

3. Lill MA, Winiger F, Vedani A, Ernst B..  (2005)  Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.,  48  (18): [PMID:16134935] [10.1021/jm050403f]

4. 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]

5. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

6. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

7. Unpublished dataset, 

8. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

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

10. Labbé C, Faini F, Villagrán C, Coll J, Rycroft DS..  (2005)  Antifungal and insect antifeedant 2-phenylethanol esters from the liverwort Balantiopsis cancellata from Chile.,  53  (2): [PMID:15656657] [10.1021/jf048935c]

11. Dosdall LM..  (2009)  Responses of the cabbage seedpod weevil, Ceutorhynchus obstrictus (Marsham) (Coleoptera: Curculionidae), to seed treatments of canola (Brassica napus L.) with the neonicotinoid compounds clothianidin and imidacloprid.,  65  (12): [PMID:19642076] [10.1002/ps.1818]

12. Argandoña VH, Rovirosa J, San-Martín A, Riquelme A, Díaz-Marrero AR, Cueto M, Darias J, Santana O, Guadaño A, González-Coloma A..  (2002)  Antifeedant effects of marine halogenated monoterpenes.,  50  (24): [PMID:12428955] [10.1021/jf025857p]

13. Gonzalez M, Miglioranza KS, Aizpún de Moreno JE, Moreno VJ..  (2003)  Occurrence and distribution of organochlorine pesticides (OCPs) in tomato (Lycopersicon esculentum) crops from organic production.,  51  (5): [PMID:12590481] [10.1021/jf025892w]

14. Casida JE, Tomizawa M.  (2008)  Insecticide interactions with -aminobutyric acid and nicotinic receptors: predictive aspects of structural models,  33  (1): [10.1584/jpestics.R07-07]

15. 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]

16. 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]

17. PubChem BioAssay data set, 

18. PubChem BioAssay data set, 

19. PubChem BioAssay data set, 

20. WHO Anatomical Therapeutic Chemical Classification, 

21. British National Formulary (72nd edition), 

22. Unpublished dataset, 

23. 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]

24. 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]

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. 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]

27. Unpublished dataset, 

Source

Source(10):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• Withdrawn Drugs
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6