alpha-IONONE
Relevant Data
Food Additives Approved in the United States
Flavouring Substances Approved by European Union:
General Information
| Synonyms: | alpha-CYCLOCITRYLIDENEACETONE |
| Chemical Names: | 4-(2,6,6-TRIMETHYL-2-CYCLOHEXENYL)-3-BUTEN-2-ONE |
| CAS number: | 127-41-3 |
| COE number: | 141 |
| JECFA number: | 388 |
| FEMA number: | 2594 |
| Functional Class: |
Flavouring Agent FLAVOURING_AGENT |
From apps.who.int
Evaluations
| Evaluation year: | 1998 |
| ADI: | 0-0.1 mg/kg bw (1984) |
| Comments: | No safety concern at current levels of intake when used as a flavouring agent. The 1984 group ADI of 0-0.1 mg/kg bw for alpha-ionone and beta-ionone, singly or in combination, was maintained at the fifty-first meeting (1998). |
| Report: | TRS 891-JECFA 51/96 |
| Tox Monograph: | FAS 42-JECFA 51/335 |
| Specification: | COMPENDIUM ADDENDUM 9/FNP 52 Add.9/118 (2001) |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 5282108 |
| IUPAC Name | (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one |
| InChI | InChI=1S/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 Key | UZFLPKAIBPNNCA-BQYQJAHWSA-N |
| Canonical SMILES | CC1=CCCC(C1C=CC(=O)C)(C)C |
| Molecular Formula | C13H20O |
| Wikipedia | alpha-ionone |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 192.302 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 2 |
| Complexity | 282.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B w I 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 g A A A A A A A A A A A A A A A A G g A A A A A A D w S A g A A C A A A A A A C I A q B S A A A A A A A g A A A I C A A A A E g A A A I A A Q A A A A A A g A A I A Y M A g A A P g 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 A A A = = |
| Topological Polar Surface Area | 17.1 |
| Monoisotopic Mass | 192.151 |
| Exact Mass | 192.151 |
| XLogP3 | None |
| XLogP3-AA | 3.0 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 1 |
| 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+ | 0.9699 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.7964 |
| P-glycoprotein Substrate | Non-substrate | 0.5373 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5796 |
| Non-inhibitor | 0.7164 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8059 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.3995 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8391 |
| CYP450 2D6 Substrate | Non-substrate | 0.8592 |
| CYP450 3A4 Substrate | Substrate | 0.6280 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7017 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8719 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9390 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8075 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9247 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6218 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9202 |
| Non-inhibitor | 0.8955 | |
| AMES Toxicity | Non AMES toxic | 0.9400 |
| Carcinogens | Non-carcinogens | 0.6772 |
| Fish Toxicity | High FHMT | 0.7238 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6432 |
| Honey Bee Toxicity | High HBT | 0.8297 |
| Biodegradation | Ready biodegradable | 0.6574 |
| Acute Oral Toxicity | III | 0.8297 |
| Carcinogenicity (Three-class) | Non-required | 0.5250 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.7995 | LogS |
| Caco-2 Permeability | 2.1163 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6526 | LD50, mol/kg |
| Fish Toxicity | 1.0689 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1381 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | |
|---|---|
| Mechanism of Toxicity | |
| Metabolism | |
| Toxicity Values | |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | |
| Health Effects | |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Sesquiterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Sesquiterpenoids |
| Alternative Parents | |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
From ClassyFire
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
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 ]
From T3DB