1-Octen-3-Ol
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Basic Info
| Common Name | 1-Octen-3-Ol(F05532) |
| 2D Structure | |
| Description | 1-Octen-3-ol, also known as mushroom alcohol is a chemical that attracts biting insects such as mosquitos. It is contained in human breath and sweat, and it was once believed that the insect repellent DEET works by blocking the insects' octenol odorant receptors. Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electronic devices. Its odor has been described as green and moldy or meaty; it is used in certain perfumes. In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism. |
| FRCD ID | F05532 |
| CAS Number | 3391-86-4 |
| PubChem CID | 2724898 |
| Formula | C8H16O |
| IUPAC Name | (3S)-oct-1-en-3-ol |
| InChI Key | VSMOENVRRABVKN-MRVPVSSYSA-N |
| InChI | InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3/t8-/m1/s1 |
| Canonical SMILES | CCCCCC(C=C)O |
| Isomeric SMILES | CCCCC[C@@H](C=C)O |
| Synonyms |
(S)-(+)-1-Octen-3-ol
(S)-1-Octen-3-ol
oct-1-en-3S-ol
(S)-oct-1-en-3-ol
24587-53-9
1-Octen-3-ol, (3S)-
UNII-07D31239FH
(3S)-oct-1-en-3-ol
VSMOENVRRABVKN-MRVPVSSYSA-N
07D31239FH
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty alcohols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Fatty alcohols |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Fatty alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 128.215 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 5 |
| Complexity | 69 |
| Monoisotopic Mass | 128.12 |
| Exact Mass | 128.12 |
| XLogP | 2.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9738 |
| Human Intestinal Absorption | HIA+ | 0.9902 |
| Caco-2 Permeability | Caco2+ | 0.8050 |
| P-glycoprotein Substrate | Non-substrate | 0.5301 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8131 |
| Non-inhibitor | 0.8647 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9016 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.3820 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7934 |
| CYP450 2D6 Substrate | Non-substrate | 0.8568 |
| CYP450 3A4 Substrate | Non-substrate | 0.6318 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7335 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8922 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8568 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9104 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7398 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8163 |
| Non-inhibitor | 0.8304 | |
| AMES Toxicity | Non AMES toxic | 0.9378 |
| Carcinogens | Non-carcinogens | 0.5423 |
| Fish Toxicity | High FHMT | 0.9414 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6953 |
| Honey Bee Toxicity | High HBT | 0.7552 |
| Biodegradation | Ready biodegradable | 0.6979 |
| Acute Oral Toxicity | II | 0.7387 |
| Carcinogenicity (Three-class) | Non-required | 0.6703 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.9838 | LogS |
| Caco-2 Permeability | 1.4600 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2858 | LD50, mol/kg |
| Fish Toxicity | 0.4555 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0149 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The anticonvulsant and anti-plasmid conjugation potential of Thymus vulgaris chemistry: An in vivo murine and in vitro study. | Food Chem Toxicol | 2018 Oct | 30055314 |
| Acaricidal activities of the active component of Lycopus lucidus oil and its derivatives against house dust and stored food mites (Arachnida: Acari). | Pest Manag Sci | 2012 Apr | 22500291 |
| Volatile compounds of Aspergillus strains with different abilities to produce ochratoxin A. | J Agric Food Chem | 2005 Mar 9 | 15740058 |
| Composition and some biological activities of the essential oil of Callicarpa americana (L.). | J Agric Food Chem | 2000 Jul | 10898657 |
| Fungal volatiles as indicators of food and feeds spoilage. | Fungal Genet Biol | 1999 Jul-Aug | 10441446 |
Targets
- 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
- 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 ]