Tmic
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Record Information
Version2.0
Creation Date2014-09-11 05:23:20 UTC
Update Date2014-12-24 20:27:00 UTC
Accession NumberT3D4940
Identification
Common Namealpha-Ionone
ClassSmall Molecule
Descriptionalpha-Ionone belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain
Compound Type
  • Ester
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Plant Toxin
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-on
(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
(E)-alpha-Ionone
a-Ionone
alpha-(E)-ionone
alpha-cyclocitrylideneacetone
alpha-Ionon
trans-alpha-Ionone
α-Ionone
Chemical FormulaC13H20O
Average Molecular Mass192.297 g/mol
Monoisotopic Mass192.151 g/mol
CAS Registry Number127-41-3
IUPAC Name(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
Traditional Nameα-ionone
SMILES[H]\C(=C(\[H])C(C)=O)C1C(C)=CCCC1(C)C
InChI IdentifierInChI=1/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
InChI KeyInChIKey=UZFLPKAIBPNNCA-BQYQJAHWNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ionone derivative
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP4.14ALOGPS
logP3.32ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.09 m³·mol⁻¹ChemAxon
Polarizability23.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4900000000-acff00e4fe614e1e5bc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-0d1ee7a07c25e0eb379aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004u-3900000000-122599cd5a3606da3858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9400000000-5525adff7c75947a3830View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-86ad4191ecec06d667ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-81ca79f706995e1f2313View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aed-2900000000-e754146e5b21f942f91eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9800000000-d19fa6227b12fe21dbc3View 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 IDHMDB59883
PubChem Compound ID5282108
ChEMBL IDNot Available
ChemSpider ID4445317
KEGG IDC12286
UniProt IDNot Available
OMIM ID
ChEBI ID32319
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4940.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
AC505.94 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 ]