EUGENOL
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | EUGENOL |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 97-53-0 |
| Regnum |
177.2800 184.1257 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 3314 |
| IUPAC Name | 2-methoxy-4-prop-2-enylphenol |
| InChI | InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 |
| InChI Key | RRAFCDWBNXTKKO-UHFFFAOYSA-N |
| Canonical SMILES | COC1=C(C=CC(=C1)CC=C)O |
| Molecular Formula | C10H12O2 |
| Wikipedia | eugenol |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 164.204 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 145.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D A S A m A I y B o A A B g C A A i B C A A A C C A A g I A A I i A A G i I g N J i K G M R q A c C M k w B E L u A e A w L A O I A A B A A A A Q A B A A A I A A A C A A A A A A A A A A A = = |
| Topological Polar Surface Area | 29.5 |
| Monoisotopic Mass | 164.084 |
| Exact Mass | 164.084 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| 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 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8736 |
| Human Intestinal Absorption | HIA+ | 0.9832 |
| Caco-2 Permeability | Caco2+ | 0.8629 |
| P-glycoprotein Substrate | Non-substrate | 0.6744 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6684 |
| Non-inhibitor | 0.6287 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8418 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7823 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7523 |
| CYP450 2D6 Substrate | Non-substrate | 0.7857 |
| CYP450 3A4 Substrate | Non-substrate | 0.6383 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5507 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8880 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8828 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5425 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5110 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8355 |
| Non-inhibitor | 0.9279 | |
| AMES Toxicity | Non AMES toxic | 0.9265 |
| Carcinogens | Non-carcinogens | 0.8432 |
| Fish Toxicity | High FHMT | 0.9431 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9663 |
| Honey Bee Toxicity | High HBT | 0.8095 |
| Biodegradation | Not ready biodegradable | 0.6080 |
| Acute Oral Toxicity | III | 0.8605 |
| Carcinogenicity (Three-class) | Non-required | 0.5959 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.9183 | LogS |
| Caco-2 Permeability | 1.4919 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9616 | LD50, mol/kg |
| Fish Toxicity | 0.8660 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3846 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | |
|---|---|
| Mechanism of Toxicity | |
| Metabolism | |
| Toxicity Values | |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. |
| Minimum Risk Level | |
| Health Effects | |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Methoxyphenols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Methoxyphenols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Methoxyphenol - Phenoxy compound - Methoxybenzene - Phenol ether - Anisole - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
From ClassyFire
Targets
- General Function:
- Calcium channel activity
- Specific Function:
- Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 degrees Celsius. Activation exhibits an outward rectification. May associate with TRPV1 and may modulate its activity. Is a negative regulator of hair growth and cycling: TRPV3-coupled signaling suppresses keratinocyte proliferation in hair follicles and induces apoptosis and premature hair follicle regression (catagen).
- Gene Name:
- TRPV3
- Uniprot ID:
- Q8NET8
- Molecular Weight:
- 90635.115 Da
References
- Borbiro I, Lisztes E, Toth BI, Czifra G, Olah A, Szollosi AG, Szentandrassy N, Nanasi PP, Peter Z, Paus R, Kovacs L, Biro T: Activation of transient receptor potential vanilloid-3 inhibits human hair growth. J Invest Dermatol. 2011 Aug;131(8):1605-14. doi: 10.1038/jid.2011.122. Epub 2011 May 19. [21593771 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [12495555 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Ogawa Y, Akamatsu M, Hotta Y, Hosoda A, Tamura H: Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2111-4. doi: 10.1016/j.bmcl.2010.02.059. Epub 2010 Feb 21. [20226658 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR: Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. [12495555 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 Da
References
- Fakhrudin N, Ladurner A, Atanasov AG, Heiss EH, Baumgartner L, Markt P, Schuster D, Ellmerer EP, Wolber G, Rollinger JM, Stuppner H, Dirsch VM: Computer-aided discovery, validation, and mechanistic characterization of novel neolignan activators of peroxisome proliferator-activated receptor gamma. Mol Pharmacol. 2010 Apr;77(4):559-66. doi: 10.1124/mol.109.062141. Epub 2010 Jan 11. [20064974 ]
From T3DB