alpha-Ionone
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Basic Info
| Common Name | Alpha-Ionone(F11807) |
| 2D Structure | |
| FRCD ID | F11807 |
| CAS Number | 127-41-3 |
| PubChem CID | 24680 |
| Formula | C13H20O |
| IUPAC Name | 4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one |
| InChI Key | UZFLPKAIBPNNCA-UHFFFAOYSA-N |
| 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 |
| Canonical SMILES | CC1=CCCC(C1C=CC(=O)C)(C)C |
| Isomeric SMILES | CC1=CCCC(C1C=CC(=O)C)(C)C |
| Synonyms |
4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
IONONE, ALPHA
.alpha.-Ionone
30685-95-1
AC1L2NLN
KSC924O8J
CTK4G5578
CTK4J5775
CTK8C4784
KS-000012ES
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| 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. |
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 |
| Monoisotopic Mass | 192.151 |
| Exact Mass | 192.151 |
| XLogP | 3 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 1 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| 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 |
| 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Chemistry of tobacco constituents. Oxidation of alpha-ionone and the acid-catalyzed rearrangement of 5-keto-alpha-ionone. | J Agric Food Chem | 1976 Jan-Feb | 1433 |
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 ]