Record Information
Version1.0
Creation date2010-04-08 22:06:10 UTC
Update date2019-11-26 02:59:55 UTC
Primary IDFDB004274
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHydantoin
DescriptionHydantoin, also known as glycolylurea or 2,4-imidazolidinedione, is a member of the class of compounds known as imidazoles. Imidazoles 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. Hydantoin is soluble (in water) and a very weakly acidic compound (based on its pKa). Hydantoin can be found in a number of food items such as cabbage, common verbena, black radish, and brazil nut, which makes hydantoin a potential biomarker for the consumption of these food products. Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to a groups and a class of compounds with the same ring structure as the parent. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule .
CAS Number461-72-3
Structure
Thumb
Synonyms
SynonymSource
2,4(3H,5H)-ImidazoledioneChEBI
2,4-ImidazolidinedioneChEBI
GlycolylureaChEBI
Imidazole-2,4(3H,5H)-dioneChEBI
Imidazolidine-2,4-dioneMeSH
2-Imidazolin-4(or 5)-one, 2-hydroxy-biospider
Dantochlorbiospider
Hydantoin Derivative 36biospider
Imidazole-2,4(3H, 5H)-dionebiospider
imidazolidine-2,4-dionebiospider
Predicted Properties
PropertyValueSource
Water Solubility36.8 g/LALOGPS
logP-1.5ALOGPS
logP-1.5ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.05 m³·mol⁻¹ChemAxon
Polarizability8.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H4N2O2
IUPAC nameimidazolidine-2,4-dione
InChI IdentifierInChI=1S/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)
InChI KeyWJRBRSLFGCUECM-UHFFFAOYSA-N
Isomeric SMILESO=C1CNC(=O)N1
Average Molecular Weight100.0761
Monoisotopic Molecular Weight100.027277382
Classification
Description Belongs to the class of organic compounds known as imidazoles. Imidazoles 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazoles
Alternative Parents
Substituents
  • Imidazole
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point220 oC
Boiling PointNot Available
Experimental Water Solubility39.7 mg/mL at 100 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.69HANSCH,C ET AL. (1995)
Experimental pKa9.12
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHydantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zor-9200000000-00dd275be69e09ff7831Spectrum
Predicted GC-MSHydantoin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-79f2feeafcde1e42f7aa2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-c6cb46642e3e5214a51c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9000000000-34a53a0f58ee15dcb29b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-9000000000-3451fd1c05a1811950232021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-90726b17dc36e29c52992021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c52992021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-d5fea3cc3a38fd5026922015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3900000000-fcab5c6b0722c56015952015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-9be606f50cf484530f232015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-542377286d0f25dd0d9d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi3-9200000000-72fe0474d06c3c95c4be2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5bf44c25d5232c7b55992021-10-12View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10006
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDHYDANTOIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).