ID: ALA485259

Max Phase: Phase

Molecular Formula: C10H18O

Molecular Weight: 154.25

Molecule Type: Small molecule

Representations

Synonyms (13): 1,8-cineol | 1,8-cineole | Cajeputol | Cineole | Eucaly | Eucalyptol | Eucalyptole | Eucapur | Eukalyptol | P-cineole | Terpan | FEMA NO. 2465 | NSC-6171
Synonyms from Alternative Forms(13):

Canonical SMILES:  CC12CCC(CC1)C(C)(C)O2

Standard InChI:  InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3

Standard InChI Key:  WEEGYLXZBRQIMU-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: 154.25

Molecular Weight (Monoisotopic): 154.1358

AlogP: 2.74

#Rotatable Bonds: 0

Polar Surface Area: 9.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 1

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.35

CX LogD: 2.35

Aromatic Rings: 0

Heavy Atoms: 11

QED Weighted: 0.52

Np Likeness Score: 2.78

References

1. Huss U, Ringbom T, Perera P, Bohlin L, Vasänge M..  (2002)  Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.,  65  (11): [PMID:12444669] [10.1021/np020023m]

2. Himejima M, Kubo I..  (1992)  Antimicrobial agents from Licaria puchuri-major and their synergistic effect with polygodial.,  55  (5): [PMID:1517735] [10.1021/np50083a010]

3. Voets T, Talavera K, Owsianik G, Nilius B..  (2005)  Sensing with TRP channels.,  1  (2): [PMID:16408004] [10.1038/nchembio0705-85]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

8. PubChem BioAssay data set, 

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

10. Ntalli NG, Ferrari F, Giannakou I, Menkissoglu-Spiroudi U..  (2010)  Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.,  58  (13): [PMID:20527965] [10.1021/jf100797m]

11. Cárdenas-Ortega NC, Zavala-Sánchez MA, Aguirre-Rivera JR, Pérez-González C, Pérez-Gutiérrez S..  (2005)  Chemical composition and antifungal activity of essential oil of Chrysactinia mexicana gray.,  53  (11): [PMID:15913293] [10.1021/jf040372h]

12. Tabanca N, Demirci B, Baser KH, Aytac Z, Ekici M, Khan SI, Jacob MR, Wedge DE..  (2006)  Chemical composition and antifungal activity of Salvia macrochlamys and Salvia recognita essential oils.,  54  (18): [PMID:16939314] [10.1021/jf0608773]

13. Kordali S, Kesdek M, Çakir A..  (2007)  Toxicity of monoterpenes against larvae and adults of Colorado potato beetle, Leptinotarsa decemlineata Say (Coleoptera: Chrysomelidae),  26  (3): [10.1016/j.indcrop.2007.03.009]

14. Kim MK, Choi GJ, Lee HS..  (2003)  Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.,  51  (6): [PMID:12617587] [10.1021/jf0210369]

15. Gonzalez-Coloma A, Martin-Benito D, Mohamed N, Garcia-Vallejo MC, Soria AC.  (2006)  Antifeedant effects and chemical composition of essential oils from different populations of Lavandula luisieri L.,  34  (8): [10.1016/j.bse.2006.02.006]

16. Araújo EC, Silveira ER, Lima MA, Neto MA, de Andrade IL, Lima MA, Santiago GM, Mesquita AL..  (2003)  Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth.,  51  (13): [PMID:12797740] [10.1021/jf021074s]

17. Han J, Kim SI, Choi BR, Lee SG, Ahn YJ..  (2011)  Fumigant toxicity of lemon eucalyptus oil constituents to acaricide-susceptible and acaricide-resistant Tetranychus urticae.,  67  (12): [PMID:21674753] [10.1002/ps.2216]

18. Tong F, Coats JR..  (2012)  Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.,  68  (8): [PMID:22461383] [10.1002/ps.3280]

19. Abdelgaleil SAM.  (2010)  Molluscicidal and insecticidal potential of monoterpenes on the white garden snail, Theba pisana (Muller) and the cotton leafworm, Spodoptera littoralis (Boisduval),  45  (3): [10.1303/aez.2010.425]

20. TAIRA S, TAWATA S, KOBAMOTO N, TOYAMA S, YASUDA M.  (1994)  Synthesis and Fungicidal Activity of New 1, 3, 2-Oxazaphospholidine 2-Sulfides,  19  (4): [10.1584/jpestics.19.4_299]

21. Jun HJ, Hoang MH, Yeo SK, Jia Y, Lee SJ..  (2013)  Induction of ABCA1 and ABCG1 expression by the liver X receptor modulator cineole in macrophages.,  23  (2): [PMID:23246324] [10.1016/j.bmcl.2012.11.012]

22. PubChem BioAssay data set, 

23. Ramos Alvarenga RF, Wan B, Inui T, Franzblau SG, Pauli GF, Jaki BU..  (2014)  Airborne antituberculosis activity of Eucalyptus citriodora essential oil.,  77  (3): [PMID:24641242] [10.1021/np400872m]

24. PubChem BioAssay data set, 

25. PubChem BioAssay data set, 

26. PubChem BioAssay data set, 

27. WHO Anatomical Therapeutic Chemical Classification, 

28. DrugMatrix,  [10.6019/CHEMBL3885881]

29. Sparling BA, DiMauro EF..  (2017)  Progress in the discovery of small molecule modulators of the Cys-loop superfamily receptors.,  27  (15): [PMID:28606760] [10.1016/j.bmcl.2017.04.073]

30. Unpublished dataset, 

31. 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]

32. 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]

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

34. Pérez de Vega MJ, Gómez-Monterrey I, Ferrer-Montiel A, González-Muñiz R..  (2016)  Transient Receptor Potential Melastatin 8 Channel (TRPM8) Modulation: Cool Entryway for Treating Pain and Cancer.,  59  (22): [PMID:27437828] [10.1021/acs.jmedchem.6b00305]

Source

Source(8):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data