Methyleugenol
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Basic Info
| Common Name | Methyleugenol(F05573) |
| 2D Structure | |
| Description | Methyleugenol is found in allspice. Methyleugenol is present in many essential oils, e.g. nutmeg, mace and also many fruits, e.g. apple, banana, orange juice or peel, grapefruit, bilberry Methyleugenol has been shown to exhibit anti-nociceptive function (A7914). Methyleugenol belongs to the family of Anisoles. These are organic compounds contaiing a methoxybenzene or a derivative thereof. |
| FRCD ID | F05573 |
| CAS Number | 93-15-2 |
| PubChem CID | 7127 |
| Formula | C11H14O2 |
| IUPAC Name | 1,2-dimethoxy-4-prop-2-enylbenzene |
| InChI Key | ZYEMGPIYFIJGTP-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 |
| Canonical SMILES | COC1=C(C=C(C=C1)CC=C)OC |
| Isomeric SMILES | COC1=C(C=C(C=C1)CC=C)OC |
| Synonyms |
4-Allyl-1,2-dimethoxybenzene
METHYLEUGENOL
Methyl eugenol
93-15-2
Eugenol methyl ether
4-Allylveratrole
O-Methyleugenol
Eugenyl methyl ether
3,4-Dimethoxyallylbenzene
Methyl eugenol ether
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Methoxybenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dimethoxybenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | O-dimethoxybenzene - Dimethoxybenzene - Phenoxy compound - Phenol ether - Anisole - Alkyl aryl ether - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 178.231 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Complexity | 156 |
| Monoisotopic Mass | 178.099 |
| Exact Mass | 178.099 |
| XLogP | 2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9385 |
| Human Intestinal Absorption | HIA+ | 0.9938 |
| Caco-2 Permeability | Caco2+ | 0.8877 |
| P-glycoprotein Substrate | Non-substrate | 0.6987 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5435 |
| Non-inhibitor | 0.6950 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8405 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7777 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8173 |
| CYP450 2D6 Substrate | Non-substrate | 0.7090 |
| CYP450 3A4 Substrate | Non-substrate | 0.5696 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7030 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9166 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8485 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6373 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7787 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6995 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8488 |
| Non-inhibitor | 0.9196 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8119 |
| Fish Toxicity | High FHMT | 0.9591 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9635 |
| Honey Bee Toxicity | High HBT | 0.8471 |
| Biodegradation | Not ready biodegradable | 0.6723 |
| Acute Oral Toxicity | III | 0.9019 |
| Carcinogenicity (Three-class) | Non-required | 0.5202 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7368 | LogS |
| Caco-2 Permeability | 1.7031 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1602 | LD50, mol/kg |
| Fish Toxicity | 0.9395 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5077 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Stable isotope labeling-assisted GC/MS/MS method for determination ofmethyleugenol in food samples. | J Sci Food Agric | 2018 Jul | 29314056 |
| Characterization of Essential Oil Composition in Different Basil Species and Pot Cultures by a GC-MS Method. | Molecules | 2017 Jul 20 | 28726757 |
| Toxicity of Plant Secondary Metabolites Modulating Detoxification Genes Expression for Natural Red Palm Weevil Pesticide Development. | Molecules | 2017 Jan 20 | 28117698 |
| Factors influencing aversive learning in the oriental fruit fly, Bactroceradorsalis. | J Comp Physiol A Neuroethol Sens Neural Behav Physiol | 2017 Jan | 27909789 |
| Determination and risk assessment of naturally occurring genotoxic and carcinogenic alkenylbenzenes in basil-containing sauce of pesto. | Toxicol Rep | 2017 | 28959619 |
| GC×GC-TOFMS Analysis of Essential Oils Composition from Leaves, Twigs and Seedsof Cinnamomum camphora L. Presl and Their Insecticidal and Repellent Activities. | Molecules | 2016 Mar 28 | 27043503 |
| The influence of the SULT1A status - wild-type, knockout or humanized - on theDNA adduct formation by methyleugenol in extrahepatic tissues of mice. | Toxicol Res (Camb) | 2016 Feb 12 | 30090391 |
| Effect of jasmonic acid elicitation on the yield, chemical composition, andantioxidant and anti-inflammatory properties of essential oil of lettuce leafbasil (Ocimum basilicum L.). | Food Chem | 2016 Dec 15 | 27451148 |
| Acaricidal activity of Asarum heterotropoides root-derived compounds and hydrodistillate constitutes toward Dermanyssus gallinae (Mesostigmata: Dermanyssidae). | Exp Appl Acarol | 2016 Apr | 26708137 |
| Structure-Activity Relationships for DNA Damage by Alkenylbenzenes in Turkey Egg Fetal Liver. | Toxicol Sci | 2016 Apr | 26719370 |
| Identification of character-impact odorants in a cola-flavored carbonatedbeverage by quantitative analysis and omission studies of aroma reconstitutionmodels. | J Agric Food Chem | 2015 Jan 28 | 25529113 |
| Pimenta pseudocaryophyllus Derivatives: Extraction Methods and BioactivityAgainst Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae). | Neotrop Entomol | 2015 Dec | 26285912 |
| Exploring the uncertainties in cancer risk assessment using the integrated probabilistic risk assessment (IPRA) approach. | Risk Anal | 2014 Aug | 24766324 |
| Comparative investigation of Umbellularia californica and Laurus nobilis leafessential oils and identification of constituents active against Aedes aegypti. | J Agric Food Chem | 2013 Dec 18 | 24266426 |
| Myrtus communis L. infusions: the effect of infusion time on phytochemicalcomposition, antioxidant, and antimicrobial activities. | J Food Sci | 2012 Sep | 22888790 |
| Trap capture of three economically important fruit fly species (Diptera:Tephritidae): evaluation of a solid formulation containing multiple male lures ina Hawaiian coffee field. | J Econ Entomol | 2012 Aug | 22928297 |
| Artemisia dracunculus L. (tarragon): a critical review of its traditional use, chemical composition, pharmacology, and safety. | J Agric Food Chem | 2011 Nov 9 | 21942448 |
| Physiologically based biokinetic (PBBK) model for safrole bioactivation anddetoxification in rats. | Chem Res Toxicol | 2011 Jun 20 | 21446753 |
| NTP 3-month toxicity studies of estragole (CAS No. 140-67-0) administered by gavage to F344/N rats and B6C3F1 mice. | Toxic Rep Ser | 2011 Jan | 21445103 |
| Myrtus communis berry color morphs: a comparative analysis of essential oils,fatty acids, phenolic compounds, and antioxidant activities. | Chem Biodivers | 2011 Feb | 21337502 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
- Gene Name:
- PPARA
- Uniprot ID:
- Q07869
- Molecular Weight:
- 52224.595 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]