ID: ALA108545

Max Phase: Approved

First Approval: 2008

Molecular Formula: C8H8O3

Molecular Weight: 152.15

Molecule Type: Small molecule

Representations

Synonyms (13): Betula oil | Birch oil, sweet | Fema no. 2154 | Fema no. 3113 | Flavor,wintergreen | Gaultheria oil | Methyl salicylate | Methyl salicylate,synthetic | Sweet birch oil | Teaberry oil | Wintergreen oil | FEMA NO. 2745 | NSC-8204
Synonyms from Alternative Forms(13):

Trade Names(15): Aspellin | Balmosa | Bengue's balsam | Deep heat | Dubam | Gppe lin | Gppe rub | Luma | Methyl Salicylate | Nasciodine | P.r. | Radian-b | Rhodiaflor | Sloans | Thera-gesic

Canonical SMILES:  COC(=O)c1ccccc1O

Standard InChI:  InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3

Standard InChI Key:  OSWPMRLSEDHDFF-UHFFFAOYSA-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: No

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 152.15

Molecular Weight (Monoisotopic): 152.0473

AlogP: 1.18

#Rotatable Bonds: 1

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.72

CX Basic pKa:

CX LogP: 2.32

CX LogD: 2.32

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.61

Np Likeness Score: 0.03

References

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3. Jones M, Inkielewicz I, Medina C, Santos-Martinez MJ, Radomski A, Radomski MW, Lally MN, Moriarty LM, Gaynor J, Carolan CG, Khan D, O'Byrne P, Harmon S, Holland V, Clancy JM, Gilmer JF..  (2009)  Isosorbide-based aspirin prodrugs: integration of nitric oxide releasing groups.,  52  (21): [PMID:19821574] [10.1021/jm900561s]

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7. Unpublished dataset, 

8. Barbosa TP, Sousa SC, Amorim FM, Rodrigues YK, de Assis PA, Caldas JP, Oliveira MR, Vasconcellos ML..  (2011)  Design, synthesis and antileishmanial in vitro activity of new series of chalcones-like compounds: a molecular hybridization approach.,  19  (14): [PMID:21684751] [10.1016/j.bmc.2011.05.055]

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

12. Teulon DA, Davidson MM, Hedderley DI, James DE, Fletcher CD, Larsen L, Green VC, Perry NB..  (2007)  4-pyridyl carbonyl and related compounds as thrips lures: effectiveness for onion thrips and new zealand flower thrips in field experiments.,  55  (15): [PMID:17602496] [10.1021/jf070389a]

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15. Ooshiro A, Kaji M, Katoh Y, Kawaide H, Natsume M.  (2011)  Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum,  36  (2): [10.1584/jpestics.G10-84]

16. 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]

17. Caboni P, Aissani N, Cabras T, Falqui A, Marotta R, Liori B, Ntalli N, Sarais G, Sasanelli N, Tocco G..  (2013)  Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita.,  61  (8): [PMID:23379671] [10.1021/jf305164m]

18. PubChem BioAssay data set, 

19. PubChem BioAssay data set, 

20. PubChem BioAssay data set, 

21. British National Formulary (72nd edition), 

22. DrugMatrix,  [10.6019/CHEMBL3885881]

23. Unpublished dataset, 

24. 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]

25. 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]

26. 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]

27. 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(9):

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