Imidazolidinyl urea (T3D3625)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2009-11-23 22:43:07 UTC
Update Date2014-12-24 20:26:14 UTC
Accession NumberT3D3625
Identification
Common NameImidazolidinyl urea
ClassSmall Molecule
DescriptionImidazolidinyl urea is an antimicrobial preservative used in cosmetics. It acts as a formaldehyde releaser. Imidazolidinyl urea may cause contact dermatitis. It's toxicity is also due to it's ability to react and release formaldehyde and nitrosamines, both of which are believed to be carcinogenic. (7, 8)
Compound Type
  • Amide
  • Cosmetic Toxin
  • Household Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
Germall 115
Imidurea
Chemical FormulaC11H16N8O8
Average Molecular Mass388.294 g/mol
Monoisotopic Mass388.109 g/mol
CAS Registry Number39236-46-9
IUPAC Name3-[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-1-[({[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]carbamoyl}amino)methyl]urea
Traditional Name3-[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-1-[({[4-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]carbamoyl}amino)methyl]urea
SMILESOCC1(NC(=O)NCNC(=O)NC2(CO)NC(=O)NC2=O)NC(=O)NC1=O
InChI IdentifierInChI=1S/C11H16N8O8/c20-1-10(4(22)14-8(26)18-10)16-6(24)12-3-13-7(25)17-11(2-21)5(23)15-9(27)19-11/h20-21H,1-3H2,(H2,12,16,24)(H2,13,17,25)(H2,14,18,22,26)(H2,15,19,23,27)
InChI KeyInChIKey=GAZOQRUEIUBTNF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as allantoins. These are heterocyclic compounds containing an imiazolidine ring substituted by a ketone group at positions 2 and 5, and an urea at position 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentAllantoins
Alternative Parents
Substituents
  • Allantoin
  • Alpha-amino acid or derivatives
  • 5-monosubstituted hydantoin
  • N-acyl urea
  • Ureide
  • Dicarboximide
  • Carbonic acid derivative
  • Urea
  • Carboxylic acid derivative
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility1000 mg/mL at 25°C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP-2.3ALOGPS
logP-4.8ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area239.12 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.44 m³·mol⁻¹ChemAxon
Polarizability33.24 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0072-2948000000-58bf7047877f08876ef92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2910000000-a4754ad69b7d80f7e6a82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004s-9600000000-70dacace856b8200d19b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0819000000-16a77d977fd1457425802016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9603000000-39e60b03d94886b3ef812016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7590000000-8ff2bbbdda36339b00592016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
Mechanism of ToxicityImidazolidinyl urea is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). Imidazolidinyl urea is also a nitrosating agent. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. Nitrosamines are produced from secondary amines and amides in the presence of nitrite ions and are believed to be carcinogenic. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. (5, 6, 7, 1, 2, 3, 8)
MetabolismFormaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. Nitrosamines can also enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. (5, 1, 2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans (for formaldehyde). (4)
Uses/SourcesImidazolidinyl urea is an antimicrobial preservative used in cosmetics. (8)
Minimum Risk LevelNot Available
Health EffectsImidazolidinyl urea releases formaldehyde, a known human carcinogen. It may also react to produce nitrosamines, which are believed to be carcinogenic. (5, 7, 8)
SymptomsSome people have a contact allergy to imidazolidinyl urea, causing dermatitis. (8)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID38258
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkImidazolidinyl_urea
References
Synthesis ReferenceNot Available
MSDST3D3625.pdf
General References
  1. Oyama T, Sugio K, Uramoto H, Iwata T, Onitsuka T, Isse T, Nozoe T, Kagawa N, Yasumoto K, Kawamoto T: Increased cytochrome P450 and aryl hydrocarbon receptor in bronchial epithelium of heavy smokers with non-small cell lung carcinoma carries a poor prognosis. Front Biosci. 2007 May 1;12:4497-503. [17485391 ]
  2. Sasaki S, Sata F, Katoh S, Saijo Y, Nakajima S, Washino N, Konishi K, Ban S, Ishizuka M, Kishi R: Adverse birth outcomes associated with maternal smoking and polymorphisms in the N-Nitrosamine-metabolizing enzyme genes NQO1 and CYP2E1. Am J Epidemiol. 2008 Mar 15;167(6):719-26. doi: 10.1093/aje/kwm360. Epub 2008 Jan 23. [18218609 ]
  3. Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. [15380096 ]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. Wikipedia. Nitrosamine. Last Updated 16 November 2009. [Link]
  7. Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
  8. Wikipedia. Imidazolidinyl urea. Last Updated 24 October 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. RNA
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  2. Wikipedia. Imidazolidinyl urea. Last Updated 24 October 2009. [Link]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Drablos F, Feyzi E, Aas PA, Vaagbo CB, Kavli B, Bratlie MS, Pena-Diaz J, Otterlei M, Slupphaug G, Krokan HE: Alkylation damage in DNA and RNA--repair mechanisms and medical significance. DNA Repair (Amst). 2004 Nov 2;3(11):1389-407. [15380096 ]
  2. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  3. Organic Natural Health (1998). Cancer Causing Toxic Chemical Ingredients in Cosmetic and Skin Care Products. [Link]
  4. Wikipedia. Imidazolidinyl urea. Last Updated 24 October 2009. [Link]