2-Ethylhexanoic acid
General Information
| Chemical name | 2-Ethylhexanoic acid |
| CAS number | 149-57-5 |
| Flavouring type | substances |
| FL No. | 08.078 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified | |
| Reference body | EFSA |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 8697 |
| IUPAC Name | 2-ethylhexanoic acid |
| InChI | InChI=1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) |
| InChI Key | OBETXYAYXDNJHR-UHFFFAOYSA-N |
| Canonical SMILES | CCCCC(CC)C(=O)O |
| Molecular Formula | C8H16O2 |
| Wikipedia | 2-ethylhexanoic acid |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 144.214 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 5 |
| Complexity | 99.4 |
| CACTVS Substructure Key Fingerprint | A A A D c e B w M 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 A A A A A A A A A A A A A A G g A A C A A A D Q C A g A A C C A A A A g A I A A C Q C A A A A A A A A A A A A A E A A A A A A B I A A A A A Q A A E A A A A A A G I y A A O 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 A = = |
| Topological Polar Surface Area | 37.3 |
| Monoisotopic Mass | 144.115 |
| Exact Mass | 144.115 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9677 |
| Human Intestinal Absorption | HIA+ | 0.9850 |
| Caco-2 Permeability | Caco2+ | 0.8856 |
| P-glycoprotein Substrate | Non-substrate | 0.6764 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9748 |
| Non-inhibitor | 0.7961 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9156 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5582 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8125 |
| CYP450 2D6 Substrate | Non-substrate | 0.9048 |
| CYP450 3A4 Substrate | Non-substrate | 0.6953 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5793 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8225 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9384 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9531 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9524 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9326 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9462 |
| Non-inhibitor | 0.9145 | |
| AMES Toxicity | Non AMES toxic | 0.9888 |
| Carcinogens | Non-carcinogens | 0.5486 |
| Fish Toxicity | High FHMT | 0.9349 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9993 |
| Honey Bee Toxicity | High HBT | 0.7030 |
| Biodegradation | Ready biodegradable | 0.8378 |
| Acute Oral Toxicity | III | 0.8829 |
| Carcinogenicity (Three-class) | Non-required | 0.6481 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8186 | LogS |
| Caco-2 Permeability | 1.4249 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7694 | LD50, mol/kg |
| Fish Toxicity | 1.5237 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2010 | 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 | Fatty Acyls |
| Subclass | Fatty acids and conjugates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Medium-chain fatty acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Medium-chain fatty acid - Branched fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
From ClassyFire
Targets
- 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
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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Key regulator of cellular differentiation, immunity, peripheral circadian rhythm as well as lipid, steroid, xenobiotics and glucose metabolism. Considered to have intrinsic transcriptional activity, have some natural ligands like oxysterols that act as agonists (25-hydroxycholesterol) or inverse agonists (7-oxygenated sterols), enhancing or repressing the transcriptional activity, respectively. Recruits distinct combinations of cofactors to target gene regulatory regions to modulate their transcriptional expression, depending on the tissue, time and promoter contexts. Regulates the circadian expression of clock genes such as CRY1, ARNTL/BMAL1 and NR1D1 in peripheral tissues and in a tissue-selective manner. Competes with NR1D1 for binding to their shared DNA response element on some clock genes such as ARNTL/BMAL1, CRY1 and NR1D1 itself, resulting in NR1D1-mediated repression or RORC-mediated activation of the expression, leading to the circadian pattern of clock genes expression. Therefore influences the period length and stability of the clock. Involved in the regulation of the rhythmic expression of genes involved in glucose and lipid metabolism, including PLIN2 and AVPR1A. Negative regulator of adipocyte differentiation through the regulation of early phase genes expression, such as MMP3. Controls adipogenesis as well as adipocyte size and modulates insulin sensitivity in obesity. In liver, has specific and redundant functions with RORA as positive or negative modulator of expression of genes encoding phase I and Phase II proteins involved in the metabolism of lipids, steroids and xenobiotics, such as SULT1E1. Also plays also a role in the regulation of hepatocyte glucose metabolism through the regulation of G6PC and PCK1. Regulates the rhythmic expression of PROX1 and promotes its nuclear localization (By similarity). Plays an indispensable role in the induction of IFN-gamma dependent anti-mycobacterial systemic immunity (PubMed:26160376).Isoform 2: Essential for thymopoiesis and the development of several secondary lymphoid tissues, including lymph nodes and Peyer's patches. Required for the generation of LTi (lymphoid tissue inducer) cells. Regulates thymocyte survival through DNA-binding on ROREs of target gene promoter regions and recruitment of coactivaros via the AF-2. Also plays a key role, downstream of IL6 and TGFB and synergistically with RORA, for lineage specification of uncommitted CD4(+) T-helper (T(H)) cells into T(H)17 cells, antagonizing the T(H)1 program. Probably regulates IL17 and IL17F expression on T(H) by binding to the essential enhancer conserved non-coding sequence 2 (CNS2) in the IL17-IL17F locus. May also play a role in the pre-TCR activation cascade leading to the maturation of alpha/beta T-cells and may participate in the regulation of DNA accessibility in the TCR-J(alpha) locus.
- Gene Name:
- RORC
- Uniprot ID:
- P51449
- Molecular Weight:
- 58194.845 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