Allantoin
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Basic Info
| Common Name | Allantoin(F05629) |
| 2D Structure | |
| Description | Allantoin is a diureide of glyoxylic acid with the chemical formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a product of purine metabolism in most mammals except higher apes, and it is present in their urine. In humans, uric acid is excreted instead of allantoin. The presence of allantoin in the urine can be an indication of microbial overgrowth or it can be created via non-enzymatic means through high levels of reactive oxygen species. In this regard Allantoin is sometimes used as a marker of oxidative stress. Allantoin can be isolated from cow urine or as a botanical extract of the comfrey plant. It has long been used for its healing, soothing, and anti-irritating properties. Allantoin helps to heal wounds and skin irritations and stimulates the growth of healthy tissue. Allantoin can be found in anti-acne products, sun care products, and clarifying lotions because of its ability to help heal minor wounds and promote healthy skin. Allantoin is frequently present in toothpaste, mouthwash, and other oral hygiene products as well as shampoos, lipsticks, various cosmetic lotions and creams and other cosmetic and pharmaceutical products. |
| FRCD ID | F05629 |
| CAS Number | 97-59-6 |
| PubChem CID | 204 |
| Formula | C4H6N4O3 |
| IUPAC Name | (2,5-dioxoimidazolidin-4-yl)urea |
| InChI Key | POJWUDADGALRAB-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11) |
| Canonical SMILES | C1(C(=O)NC(=O)N1)NC(=O)N |
| Isomeric SMILES | C1(C(=O)NC(=O)N1)NC(=O)N |
| Wikipedia | Allantoin |
| Synonyms |
5-Ureidohydantoin
1-(2,5-dioxoimidazolidin-4-yl)urea
allantoin
97-59-6
Glyoxyldiureide
Glyoxyldiureid
Allantol
Cordianine
Sebical
Alantan
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Azoles |
| Subclass | Imidazoles |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Imidazoles |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Imidazole - Isourea - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Carboximidic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Imine - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as imidazoles. These are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 158.117 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 225 |
| Monoisotopic Mass | 158.044 |
| Exact Mass | 158.044 |
| XLogP | -2.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9655 |
| Human Intestinal Absorption | HIA+ | 0.9419 |
| Caco-2 Permeability | Caco2- | 0.6238 |
| P-glycoprotein Substrate | Non-substrate | 0.7429 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9357 |
| Non-inhibitor | 0.9964 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9592 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4297 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8170 |
| CYP450 2D6 Substrate | Non-substrate | 0.7483 |
| CYP450 3A4 Substrate | Non-substrate | 0.8115 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9529 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9470 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9425 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9445 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9965 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9851 |
| Non-inhibitor | 0.9631 | |
| AMES Toxicity | Non AMES toxic | 0.6948 |
| Carcinogens | Non-carcinogens | 0.9194 |
| Fish Toxicity | Low FHMT | 0.9042 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6315 |
| Honey Bee Toxicity | Low HBT | 0.7969 |
| Biodegradation | Ready biodegradable | 0.5000 |
| Acute Oral Toxicity | III | 0.6002 |
| Carcinogenicity (Three-class) | Non-required | 0.6942 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.5506 | LogS |
| Caco-2 Permeability | 0.2507 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7973 | LD50, mol/kg |
| Fish Toxicity | 3.0522 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1170 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Identification of Urinary Food Intake Biomarkers for Milk, Cheese, and Soy-Based Drink by Untargeted GC-MS and NMR in Healthy Humans. | J Proteome Res | 2017 Sep 1 | 28753012 |
| Towards natural mimetics of metformin and rapamycin. | Aging (Albany NY) | 2017 Nov 15 | 29165314 |
| Chemical composition of alfalfa silage with waste date and its feeding effect on ruminal fermentation characteristics and microbial protein synthesis in sheep. | J Anim Physiol Anim Nutr (Berl) | 2017 Jun | 27600493 |
| Changes in the metabolome of rats after exposure to arginine andN-carbamylglutamate in combination with diquat, a compound that causes oxidative stress, assessed by 1H NMR spectroscopy. | Food Funct | 2016 Feb | 26732548 |
| Allantoin Increases Cadmium Tolerance in Arabidopsis via Activation ofAntioxidant Mechanisms. | Plant Cell Physiol | 2016 Dec | 27742885 |
| Antidiabetic Effects of Yam (Dioscorea batatas) and Its Active Constituent,Allantoin, in a Rat Model of Streptozotocin-Induced Diabetes. | Nutrients | 2015 Oct 15 | 26501316 |
| Response of lactating cows to live yeast supplementation during summer. | J Dairy Sci | 2015 Jun | 25795491 |
| Generation of semicarbazide from natural azine development in foods, followed by reaction with urea compounds. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2015 | 26140456 |
| Effects on milk urea concentration, urine output, and drinking water intake from incremental doses of potassium bicarbonate fed to mid-lactation dairy cows. | J Dairy Sci | 2014 Jul | 24835966 |
| Structural and functional insights into the catalytic inactivity of the majorfraction of buffalo milk xanthine oxidoreductase. | PLoS One | 2014 Jan 31 | 24498153 |
| Diet-induced hyperinsulinemia differentially affects glucose and proteinmetabolism: a high-throughput metabolomic approach in rats. | J Physiol Biochem | 2013 Sep | 23334844 |
| Biological system responses to zearalenone mycotoxin exposure by integrated metabolomic studies. | J Agric Food Chem | 2013 Nov 20 | 24164354 |
| Rapid detection of economic adulterants in fresh milk by liquidchromatography-tandem mass spectrometry. | J Chromatogr A | 2013 May 3 | 23540766 |
| Nanoparticulate silver increases uric acid and allantoin excretion in rats, asidentified by metabolomics. | J Appl Toxicol | 2012 Nov | 22610381 |
| allB, allantoin utilisation and Salmonella enterica serovar Enteritidis andTyphimurium colonisation of poultry and mice. | Folia Microbiol (Praha) | 2011 May | 21611691 |
| Nitric oxide metabolites induced in Anopheles stephensi control malaria parasite infection. | Free Radic Biol Med | 2007 Jan 1 | 17157200 |
| Bacterial protein meal in diets for pigs and minks: comparative studies onprotein turnover rate and urinary excretion of purine base derivatives. | Arch Anim Nutr | 2007 Dec | 18069615 |
| Suppressive effect of viscous dietary fiber on elevations of uric acid in serumand urine induced by dietary RNA in rats is associated with strength ofviscosity. | Int J Vitam Nutr Res | 2003 Oct | 14639801 |
| Effects of diet, level of intake, sodium bicarbonate and monensin on urinaryallantoin excretion in sheep. | Br J Nutr | 1992 May | 1320403 |
| Nickel as a micronutrient element for plants. | Biofactors | 1988 Jan | 3076427 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
- Gene Name:
- PPARA
- Uniprot ID:
- Q07869
- Molecular Weight:
- 52224.595 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 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 ]