| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-09-11 05:18:17 UTC |
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| Update Date | 2016-11-09 01:09:13 UTC |
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| Accession Number | CHEM003786 |
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| Identification |
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| Common Name | Glycoluril |
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| Class | Small Molecule |
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| Description | Glycoluril is a nitrogenous substance obtained by the reduction of allantoin. Glycoluril can be used to make Cucurbiturils. Cucurbiturils are macrocyclic molecules made of glycoluril (=C4H2N4O2=) monomers linked by methylene bridges. They have been used by chemists for various applications, including drug delivery, asymmetric synthesis, molecular switching, and dye tuning. |
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| Contaminant Sources | - HPV EPA Chemicals
- T3DB toxins
- ToxCast & Tox21 Chemicals
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| Contaminant Type | - Amide
- Amine
- Dye
- Industrial/Workplace Toxin
- Organic Compound
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| GLYCOLURIL | ChEBI |
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| Chemical Formula | C4H6N4O2 |
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| Average Molecular Mass | 142.116 g/mol |
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| Monoisotopic Mass | 142.049 g/mol |
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| CAS Registry Number | 496-46-8 |
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| IUPAC Name | (3as,6as)-octahydroimidazo[4,5-d]imidazolidine-2,5-dione |
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| Traditional Name | glycoluril |
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| SMILES | O=C1N[C@@H]2NC(=O)N[C@@H]2N1 |
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| InChI Identifier | InChI=1S/C4H6N4O2/c9-3-5-1-2(7-3)8-4(10)6-1/h1-2H,(H2,5,7,9)(H2,6,8,10)/t1-,2+ |
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| InChI Key | VPVSTMAPERLKKM-XIXRPRMCSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as imidazolines. These are organic compounds containing an imidazoline ring, which is an unsaturated ring (derived from imidazole) with two nitrogen atoms at positions 1 and 3 respectively, and containing only one CN double bond. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Azolines |
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| Sub Class | Imidazolines |
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| Direct Parent | Imidazolines |
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| Alternative Parents | |
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| Substituents | - 2-imidazoline
- Isourea
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-7ffe9a85e889bee5c036 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-1900000000-eb6c20b484814849d102 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004l-3900000000-142bb470011557336a66 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-ff7f3dcdf9d02d9802dc | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-7900000000-d11e297bd4e04a4d116f | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-912d224b71c9ba1926f0 | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Glycoluril can be used to make Cucurbiturils. They have been used by chemists for various applications, including drug delivery, asymmetric synthesis, molecular switching, and dye tuning. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB03533 |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | GLL |
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| Wikipedia Link | Not Available |
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| Chemspider ID | Not Available |
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| ChEBI ID | 37083 |
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| PubChem Compound ID | Not Available |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Ludwig Rottmaier, Rudolf Merten, “Glycoluril salts and a process for the preparation thereof.” U.S. Patent US4433144, issued December, 1972. |
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| MSDS | Not Available |
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| General References | Not Available |
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