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Isoeugenol (T3D4880)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (4)XML
Targets (4)
Record Information
Version2.0
Creation Date2014-09-11 05:20:36 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4880
Identification
Common NameIsoeugenol
ClassSmall Molecule
DescriptionIsoeugenol is is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil and cinnamon. It is very slightly soluble in water and soluble in organic solvents. It has a spicy odor and taste of clove. Isoeugenol is prepared from eugenol by heating. Eugenol is used in perfumeries, flavorings, essential oils and in medicine (local antiseptic and analgesic). It is used in the production of isoeugenol for the manufacture of vanillin. Eugenol derivatives or methoxyphenol derivatives in wider classification are used in perfumery and flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Isoeugenol is used in manufacturing perfumeries, flavorings, essential oils (odor description: Clove, spicy, sweet, woody) and in medicine (local antiseptic and analgesic) as well as vanillin. (1).
Compound Type
  • Ether
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Plastic
  • Solvent
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(E)-2-methoxy-4- (1-propenyl)-Phenol
(E)-2-methoxy-4-(1-propenyl)-Phenol
(E)-2-Methoxy-4-(prop-1-enyl)phenol
(E)-2-methoxy-4-propenyl-Phenol
(e)-isoeugenol
1-(3-Methoxy-4-hydroxyphenyl)-1-propane
1-Hydroxy-2-methoxy-4-propen-1-ylbenzene
2-Methoxy-4-(1-propenyl)-Phenol
2-Methoxy-4-(1-propenyl)phenol
2-Methoxy-4-propenyl-Phenol
2-Methoxy-4-propenylphenol
2-Methoxy-4-[(1E)-1-propenyl]phenol
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol
3-Methoxy-4-hydroxy-1-propen-1-ylbenzene
3-Methoxy-4-hydroxypropenylbenzene
4-Hydroxy-3-methoxy-1-propen-1-ylbenzene
4-Hydroxy-3-methoxy-1-propenylbenzene
4-Hydroxy-3-methoxypropenylbenzene
Isoeugenol (I)
Isoeugenol trans-form
Propenylgualacol
trans-2-Methoxy-4-propenylphenol
trans-4-Propenylgualacol
Trans-isoeugenol
Trans-p-propenylquaiacol
Chemical FormulaC10H12O2
Average Molecular Mass164.201 g/mol
Monoisotopic Mass164.084 g/mol
CAS Registry Number97-54-1
IUPAC Name2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
Traditional Nameisoeugenol
SMILES[H]\C(C)=C(\[H])C1=CC(OC)=C(O)C=C1
InChI IdentifierInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
InChI KeyInChIKey=BJIOGJUNALELMI-ONEGZZNKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • 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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-10 °C
Boiling PointNot Available
SolubilityNot Available
LogP3.04
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.79ALOGPS
logP2.64ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.86 m³·mol⁻¹ChemAxon
Polarizability18.3 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ds-1900000000-54cb7bf6efac012f1f93View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7790000000-39afffdef59235ab22a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-976746f8642ed9cede8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-aeeef853384070786115View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-28c3454817ba3f918700View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ba4c51d900ead0baa741View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b71be30e0aefb9374dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-4900000000-dc2d63615991af22ecd9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB05802
PubChem Compound ID853433
ChEMBL IDCHEMBL193598
ChemSpider ID21106129
KEGG IDC10469
UniProt IDNot Available
OMIM ID
ChEBI ID50545
BioCyc IDISOEUGENOL
CTD IDNot Available
Stitch IDNot Available
PDB IDEUG
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceMannich, C.; Schmitt, Frida. Synthesis of amino alcohols from isosafrole, isoeugenol and anethole. Arch. Pharm. (1928), 266 73-84. CAN 22:39242 AN 1928:39242
MSDSLink
General References
  1. Atsumi T, Fujisawa S, Tonosaki K: A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. Toxicol In Vitro. 2005 Dec;19(8):1025-33. Epub 2005 Jun 17. [15964168 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Estrogen receptor
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.00118 uMTox21_ERa_LUC_BG1_AgonistTox21/NCGC
References
  1. 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 ]
Target Details
2. cGMP-specific 3',5'-cyclic phosphodiesterase
General Function:
Metal ion binding
Specific Function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, PubMed:15489334). Specifically regulates nitric-oxide-generated cGMP (PubMed:15489334).
Gene Name:
PDE5A
Uniprot ID:
O76074
Molecular Weight:
99984.14 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.18 uMNVS_ENZ_hPDE5Novascreen
References
  1. 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 ]
Target Details
3. Sodium-dependent dopamine transporter
General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.31 uMNVS_TR_hDATNovascreen
References
  1. 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 ]
Target Details
4. Nuclear receptor subfamily 1 group I member 2
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.68 uMATG_PXR_TRANSAttagene
References
  1. 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 ]