Diethanolamine
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Basic Info
| Common Name | Diethanolamine(F05547) |
| 2D Structure | |
| Description | Diethanolamine, often abbreviated as DEA, is an organic chemical compound which is both a secondary amine and a dialcohol. A dialcohol has two hydroxyl groups in its molecule. Like other amines, diethanolamine acts as a weak base. Diethanolamine is widely used in the preparation of diethanolamides and diethanolamine salts of long-chain fatty acids that are formulated into soaps and surfactants used in liquid laundry and dishwashing detergents, cosmetics, shampoos, and hair conditioners. Diethanolamine is also used in textile processing, in industrial gas purification to remove acid gases, as an anticorrosion agent in metalworking fluids, and in preparations of agricultural chemicals. Aqueous diethanolamine solutions are used as solvents for numerous drugs that are administered intravenously. |
| FRCD ID | F05547 |
| CAS Number | 111-42-2 |
| PubChem CID | 8113 |
| Formula | C4H11NO2 |
| IUPAC Name | 2-(2-hydroxyethylamino)ethanol |
| InChI Key | ZBCBWPMODOFKDW-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2 |
| Canonical SMILES | C(CO)NCCO |
| Isomeric SMILES | C(CO)NCCO |
| Wikipedia | Diethanolamine |
| Synonyms |
N,N-Diethanolamine
DIETHANOLAMINE
2,2'-Iminodiethanol
111-42-2
Diolamine
Iminodiethanol
Bis(2-hydroxyethyl)amine
Diethylolamine
Diethanolamin
2,2'-Dihydroxydiethylamine
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Amines |
| Intermediate Tree Nodes | Alkanolamines |
| Direct Parent | 1,2-aminoalcohols |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | 1,2-aminoalcohol - Secondary amine - Secondary aliphatic amine - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 105.137 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Complexity | 28.9 |
| Monoisotopic Mass | 105.079 |
| Exact Mass | 105.079 |
| XLogP | -1.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| 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- | 0.5676 |
| Human Intestinal Absorption | HIA+ | 0.8838 |
| Caco-2 Permeability | Caco2- | 0.5263 |
| P-glycoprotein Substrate | Non-substrate | 0.5248 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9441 |
| Non-inhibitor | 0.8358 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7828 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7743 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8449 |
| CYP450 2D6 Substrate | Non-substrate | 0.7818 |
| CYP450 3A4 Substrate | Non-substrate | 0.7991 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8633 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9512 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9541 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9384 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9615 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9690 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Strong inhibitor | 0.6313 |
| Non-inhibitor | 0.8393 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.7699 |
| Fish Toxicity | Low FHMT | 0.8507 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9838 |
| Honey Bee Toxicity | Low HBT | 0.5952 |
| Biodegradation | Ready biodegradable | 0.7563 |
| Acute Oral Toxicity | III | 0.8481 |
| Carcinogenicity (Three-class) | Non-required | 0.7333 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.0938 | LogS |
| Caco-2 Permeability | 0.7853 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8845 | LD50, mol/kg |
| Fish Toxicity | 3.5479 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.9153 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effect of diisopropanolamine upon choline uptake and phospholipid synthesis in Chinese hamster ovary cells. | Food Chem Toxicol | 2008 Feb | 17988777 |
| Repeated dose toxicity and developmental toxicity of diisopropanolamine to rats. | Food Chem Toxicol | 2007 Oct | 17507134 |
| Absorption, distribution, metabolism and excretion of intravenously and dermally administered triethanolamine in mice. | Food Chem Toxicol | 2000 Nov | 11038241 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 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 ]