4-Allyl-2-methoxy-phenol

ID: ALA42710

Chembl Id: CHEMBL42710

Cas Number: 97-53-0

PubChem CID: 3314

Product Number: E113085

Max Phase: Early Phase

Molecular Formula: C10H12O2

Molecular Weight: 164.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-allylcatechol 2-methyl ether | Bioxeda | Caryophillic acid | Dentogum | Eugenol | FEMA NO. 2467 | NSC-209525 | NSC-8895 | eugenol|97-53-0|4-Allyl-2-methoxyphenol|4-Allylguaiacol|Eugenic acid|Allylguaiacol|p-Eugenol|Caryophyllic acid|p-Allylguaiacol|2-Methoxy-4-prop-2-enylphenol|2-Methoxy-4-allylphenol|Engenol|Phenol, 2-methoxy-4-(2-propenyl)-|1,3,4-Eugenol|2-Methoxy-4-(2-propenyl)phenol|5-Allylguaiacol|Synthetic eugenol|1-Hydroxy-2-methoxy-4-allylbenzene|4-Allylcatechol-2-methyl ether|2-MethoxShow More⌵

Canonical SMILES:  C=CCc1ccc(O)c(OC)c1

Standard InChI:  InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

Standard InChI Key:  RRAFCDWBNXTKKO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA42710

   EUGENOL

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

Calculated Properties

Molecular Weight: 164.20

Molecular Weight (Monoisotopic): 164.0837

AlogP: 2.13

#Rotatable Bonds: 3

Polar Surface Area: 29.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.94

CX Basic pKa:

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.69

Np Likeness Score: 1.05

References

1. Smith PA, Sorich MJ, McKinnon RA, Miners JO..  (2003)  Pharmacophore and quantitative structure-activity relationship modeling: complementary approaches for the rationalization and prediction of UDP-glucuronosyltransferase 1A4 substrate selectivity.,  46  (9): [PMID:12699380] [10.1021/jm020397c]

2. Matsuda H, Morikawa T, Managi H, Yoshikawa M..  (2003)  Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells.,  13  (19): [PMID:12951092] [10.1016/s0960-894x(03)00710-8]

3. Matsuda H, Ando S, Morikawa T, Kataoka S, Yoshikawa M..  (2005)  Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages.,  15  (7): [PMID:15780639] [10.1016/j.bmcl.2005.01.070]

4. Sadeghian H, Seyedi SM, Saberi MR, Arghiani Z, Riazi M..  (2008)  Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors.,  16  (2): [PMID:17998164] [10.1016/j.bmc.2007.10.016]

5. Collins DO, Gallimore WA, Reynolds WF, Williams LA, Reese PB..  (2000)  New skeletal sesquiterpenoids, caprariolides A-D, from Capraria biflora and their insecticidal activity.,  63  (11): [PMID:11087595] [10.1021/np000280w]

6. Chogo JB, Crank G..  (1981)  Chemical composition and biological activity of the Tanzanian plant Ocimum suave.,  44  (3): [PMID:6114991] [10.1021/np50015a012]

7. Kubo I, Muroi H, Kubo A..  (1994)  Naturally occurring antiacne agents.,  57  (1): [PMID:8158169] [10.1021/np50103a002]

8. Perrucci S, Macchioni G, Cioni PL, Flamini G, Morelli I..  (1995)  Structure/activity relationship of some natural monoterpenes as acaricides against Psoroptes cuniculi.,  58  (8): [PMID:7595592] [10.1021/np50122a018]

9. Sadeghian H, Attaran N, Jafari Z, Saberi MR, Seyedi SM, Eshghi H, Pordel M, Riazi MM..  (2009)  Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them.,  17  (6): [PMID:19251422] [10.1016/j.bmc.2009.02.009]

10. Kikuzaki H, Miyajima Y, Nakatani N..  (2008)  Phenolic glycosides from berries of Pimenta dioica.,  71  (5): [PMID:18314960] [10.1021/np0705615]

11. Zacchino SA, López SN, Pezzenati GD, Furlán RL, Santecchia CB, Muñoz L, Giannini FA, Rodríguez AM, Enriz RD..  (1999)  In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes.,  62  (10): [PMID:10543891] [10.1021/np9805443]

12. Kubo I, Muroi H, Himejima M..  (1993)  Combination effects of antifungal nagilactones against Candida albicans and two other fungi with phenylpropanoids.,  56  (2): [PMID:8463795] [10.1021/np50092a006]

13. 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]

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

15. Larsson J, Gottfries J, Bohlin L, Backlund A..  (2005)  Expanding the ChemGPS chemical space with natural products.,  68  (7): [PMID:16038536] [10.1021/np049655u]

16. Zheng GQ, Kenney PM, Lam LK..  (1992)  Sesquiterpenes from clove (Eugenia caryophyllata) as potential anticarcinogenic agents.,  55  (7): [PMID:1402962] [10.1021/np50085a029]

17. Podobnik B, Stojan J, Lah L, Krasevec N, Seliskar M, Rizner TL, Rozman D, Komel R..  (2008)  CYP53A15 of Cochliobolus lunatus, a target for natural antifungal compounds.,  51  (12): [PMID:18505250] [10.1021/jm800030e]

18. Seyedi SM, Eshghi H, Jafari Z, Attaran N, Sadeghian H, Saberi MR, Riazi MM..  (2009)  Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors.,  17  (4): [PMID:19157886] [10.1016/j.bmc.2008.12.065]

19. Ogawa Y, Akamatsu M, Hotta Y, Hosoda A, Tamura H..  (2010)  Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay.,  20  (7): [PMID:20226658] [10.1016/j.bmcl.2010.02.059]

20. PubChem BioAssay data set, 

21. PubChem BioAssay data set, 

22.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

23. PubChem BioAssay data set, 

24. PubChem BioAssay data set, 

25. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

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

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

28. 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]

29. Arango V, Dominguez JJ, Cardona W, Robledo SM, Munoz DL, Figadere B, Saez J.  (2012)  Synthesis and leishmanicidal activity of quinolinetriclosan and quinolineeugenol hybrids,  21  (11): [10.1007/s00044-011-9886-8]

30. Thobunluepop P..  (2009)  Implementation of bio-fungicides and seed treatment in organic rice cv. KDML 105 farming.,  12  (16): [PMID:19899322] [10.3923/pjbs.2009.1119.1126]

31. Lee S, Park B, Kim M, Choi W, Kim H, Cho K, Lee S, Lee H.  (2001)  Fungicidal activity of pipernonaline, a piperidine alkaloid derived from long pepper, Piper longum L., against phytopathogenic fungi,  20  (6): [10.1016/S0261-2194(00)00172-1]

32. Li J, Yu Y, Wang Q, Zhang J, Yang Y, Li B, Zhou X, Niu J, Wei X, Liu X, Liu Z.  (2012)  Synthesis of aspirin eugenol ester and its biological activity,  21  (7): [10.1007/s00044-011-9609-1]

33. Park IK, Lee HS, Lee SG, Park JD, Ahn YJ..  (2000)  Insecticidal and fumigant activities of Cinnamomum cassia bark-derived materials against Mechoris ursulus (Coleoptera: attelabidae).,  48  (6): [PMID:10888580] [10.1021/jf9904160]

34. Akhtar Y, Yu Y, Isman MB, Plettner E..  (2010)  Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, Trichoplusia ni: potential insect behavior control agents.,  58  (8): [PMID:20225858] [10.1021/jf9045123]

35. Kim EH, Kim HK, Ahn YJ..  (2003)  Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).,  51  (4): [PMID:12568544] [10.1021/jf0208278]

36. 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]

37. 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]

38. 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]

39. TAWATA S, TAIRA S, KOBAMOTO N, ISHIHARA M, TOYAMA S.  (1996)  Synthesis and Fungicidal Activity of New Thiophosphorylated Monoterpenoids and Related Compounds,  21  (2): [10.1584/jpestics.21.141]

40. 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]

41. PubChem BioAssay data set, 

42. PubChem BioAssay data set, 

43. PubChem BioAssay data set, 

44. de Morais SM, Vila-Nova NS, Bevilaqua CM, Rondon FC, Lobo CH, de Alencar Araripe Noronha Moura A, Sales AD, Rodrigues AP, de Figuereido JR, Campello CC, Wilson ME, de Andrade HF..  (2014)  Thymol and eugenol derivatives as potential antileishmanial agents.,  22  (21): [PMID:25281268] [10.1016/j.bmc.2014.08.020]

45. Irfan M, Aneja B, Yadava U, Khan SI, Manzoor N, Daniliuc CG, Abid M..  (2015)  Synthesis, QSAR and anticandidal evaluation of 1,2,3-triazoles derived from naturally bioactive scaffolds.,  93  [PMID:25686593] [10.1016/j.ejmech.2015.02.007]

46. PubChem BioAssay data set, 

47. IC50 data for the L-type calcium channel extracted from a set of literature articles, 

48.  (2013)  Agent for inhibiting odor of pyrazine derivatives, 

49. Haranahalli K, Tong S, Ojima I..  (2016)  Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.,  24  (24): [PMID:27189886] [10.1016/j.bmc.2016.05.003]

50. Romero-Benavides JC, Ruano AL, Silva-Rivas R, Castillo-Veintimilla P, Vivanco-Jaramillo S, Bailon-Moscoso N..  (2017)  Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies.,  129  [PMID:28231520] [10.1016/j.ejmech.2017.02.005]

51. Sharma V, Amarnath N, Shukla S, Ayana R, Kumar N, Yadav N, Kannan D, Sehrawat S, Pati S, Lochab B, Singh S..  (2018)  Benzoxazine derivatives of phytophenols show anti-plasmodial activity via sodium homeostasis disruption.,  28  (9): [PMID:29615339] [10.1016/j.bmcl.2018.03.047]

52. Charan Raja MR, Velappan AB, Chellappan D, Debnath J, Kar Mahapatra S..  (2017)  Eugenol derived immunomodulatory molecules against visceral leishmaniasis.,  139  [PMID:28826085] [10.1016/j.ejmech.2017.08.030]

53. Teixeira RR, Gazolla PAR, da Silva AM, Borsodi MPG, Bergmann BR, Ferreira RS, Vaz BG, Vasconcelos GA, Lima WP..  (2018)  Synthesis and leishmanicidal activity of eugenol derivatives bearing 1,2,3-triazole functionalities.,  146  [PMID:29407957] [10.1016/j.ejmech.2018.01.046]

54. Martelli G, Giacomini D..  (2018)  Antibacterial and antioxidant activities for natural and synthetic dual-active compounds.,  158  [PMID:30205261] [10.1016/j.ejmech.2018.09.009]

55. Badolato M, Carullo G, Cione E, Aiello F, Caroleo MC..  (2017)  From the hive: Honey, a novel weapon against cancer.,  142  [PMID:28797675] [10.1016/j.ejmech.2017.07.064]

56. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

57. Chandrabalan A, McPhillie MJ, Morice AH, Boa AN, Sadofsky LR..  (2019)  N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.,  170  [PMID:30878828] [10.1016/j.ejmech.2019.02.074]

58. Scharnow AM, Solinski AE, Wuest WM..  (2019)  Targeting S. mutans biofilms: a perspective on preventing dental caries.,  10  (7): [PMID:31391878] [10.1039/C9MD00015A]

59. Sinha S, Doble M, Manju SL..  (2019)  5-Lipoxygenase as a drug target: A review on trends in inhibitors structural design, SAR and mechanism based approach.,  27  (17): [PMID:31331653] [10.1016/j.bmc.2019.06.040]

60. Sadeghi S, Davoodvandi A, Pourhanifeh MH, Sharifi N, ArefNezhad R, Sahebnasagh R, Moghadam SA, Sahebkar A, Mirzaei H..  (2019)  Anti-cancer effects of cinnamon: Insights into its apoptosis effects.,  178  [PMID:31195168] [10.1016/j.ejmech.2019.05.067]

61. 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]

62. 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]

63. Awolade P, Cele N, Kerru N, Gummidi L, Oluwakemi E, Singh P..  (2020)  Therapeutic significance of β-glucuronidase activity and its inhibitors: A review.,  187  [PMID:31835168] [10.1016/j.ejmech.2019.111921]

64. Iwata H,Kanda N,Araki M,Sagae Y,Masuda K,Okuno Y.  (2021)  Discovery of natural TRPA1 activators through pharmacophore-based virtual screening and a biological assay.,  31  [PMID:33129991] [10.1016/j.bmcl.2020.127639]

65. San TT,Wang YH,Hu DB,Yang J,Zhang DD,Xia MY,Yang XF,Yang YP.  (2021)  A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar.,  31  [PMID:33207281] [10.1016/j.bmcl.2020.127682]

66. Ashooriha M, Khoshneviszadeh M, Khoshneviszadeh M, Rafiei A, Kardan M, Yazdian-Robati R, Emami S..  (2020)  Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors.,  201  [PMID:32652434] [10.1016/j.ejmech.2020.112480]

67. Bittencourt-Mernak MI, Pinheiro NM, da Silva RC, Ponci V, Banzato R, Pinheiro AJMCR, Olivo CR, Tibério IFLC, Lima Neto LG, Santana FPR, Lago JHG, Prado CM..  (2021)  Effects of Eugenol and Dehydrodieugenol B from Nectandra leucantha against Lipopolysaccharide (LPS)-Induced Experimental Acute Lung Inflammation.,  84  (8.0): [PMID:34264084] [10.1021/acs.jnatprod.1c00386]

68. Unpublished dataset, 

69. Christy MP, Uekusa Y, Gerwick L, Gerwick WH..  (2021)  Natural Products with Potential to Treat RNA Virus Pathogens Including SARS-CoV-2.,  84  (1.0): [PMID:33352046] [10.1021/acs.jnatprod.0c00968]

70. Goswami L, Gupta L, Paul S, Vermani M, Vijayaraghavan P, Bhattacharya AK..  (2022)  Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus.,  13  (8.0): [PMID:36092146] [10.1039/d2md00138a]

71. Kumar G, Kiran Tudu A..  (2023)  Tackling multidrug-resistant Staphylococcus aureus by natural products and their analogues acting as NorA efflux pump inhibitors.,  80  [PMID:36731248] [10.1016/j.bmc.2023.117187]

72. 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]

73. Puhl AC, Fernandes RS, Godoy AS, Gil LHVG, Oliva G, Ekins S..  (2023)  The protein disulfide isomerase inhibitor 3-methyltoxoflavin inhibits Chikungunya virus.,  83  [PMID:36940609] [10.1016/j.bmc.2023.117239]

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• Patent Bioactivity Data
• SARS-CoV-2 Screening Data 2020-21