Hmdb loader
Survey
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 11:33:43 UTC
Update Date2021-10-01 22:01:26 UTC
HMDB IDHMDB0253235
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydantoin
DescriptionHydantoin, also known as glycolylurea, 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. Hydantoin has been detected, but not quantified in, several different foods, such as evening primroses (Oenothera biennis), herbs and spices, chia (Salvia hispanica), chinese water chestnuts (Eleocharis dulcis), and chicory leaves (Cichorium intybus var. foliosum). This could make hydantoin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Hydantoin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hydantoin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hydantoin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
2,4(3H,5H)-ImidazoledioneChEBI
2,4-ImidazolidinedioneChEBI
GlycolylureaChEBI
Imidazole-2,4(3H,5H)-dioneChEBI
Imidazolidine-2,4-dioneMeSH
Chemical FormulaC3H4N2O2
Average Molecular Weight100.0761
Monoisotopic Molecular Weight100.027277382
IUPAC Nameimidazolidine-2,4-dione
Traditional Namehydantoin
CAS Registry NumberNot Available
SMILES
O=C1CNC(=O)N1
InChI Identifier
InChI=1S/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)
InChI KeyWJRBRSLFGCUECM-UHFFFAOYSA-N
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+125.06130932474
DeepCCS[M-H]-123.07230932474
DeepCCS[M-2H]-158.91130932474
DeepCCS[M+Na]+133.31830932474
AllCCS[M+H]+121.932859911
AllCCS[M+H-H2O]+116.932859911
AllCCS[M+NH4]+126.532859911
AllCCS[M+Na]+127.932859911
AllCCS[M-H]-116.232859911
AllCCS[M+Na-2H]-119.432859911
AllCCS[M+HCOO]-122.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HydantoinO=C1CNC(=O)N12706.6Standard polar33892256
HydantoinO=C1CNC(=O)N11003.4Standard non polar33892256
HydantoinO=C1CNC(=O)N11338.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydantoin,1TMS,isomer #1C[Si](C)(C)N1CC(=O)NC1=O1480.3Semi standard non polar33892256
Hydantoin,1TMS,isomer #1C[Si](C)(C)N1CC(=O)NC1=O1403.9Standard non polar33892256
Hydantoin,1TMS,isomer #1C[Si](C)(C)N1CC(=O)NC1=O2564.8Standard polar33892256
Hydantoin,1TMS,isomer #2C[Si](C)(C)N1C(=O)CNC1=O1466.3Semi standard non polar33892256
Hydantoin,1TMS,isomer #2C[Si](C)(C)N1C(=O)CNC1=O1376.2Standard non polar33892256
Hydantoin,1TMS,isomer #2C[Si](C)(C)N1C(=O)CNC1=O2592.8Standard polar33892256
Hydantoin,2TMS,isomer #1C[Si](C)(C)N1CC(=O)N([Si](C)(C)C)C1=O1403.4Semi standard non polar33892256
Hydantoin,2TMS,isomer #1C[Si](C)(C)N1CC(=O)N([Si](C)(C)C)C1=O1462.9Standard non polar33892256
Hydantoin,2TMS,isomer #1C[Si](C)(C)N1CC(=O)N([Si](C)(C)C)C1=O1788.2Standard polar33892256
Hydantoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC(=O)NC1=O1657.9Semi standard non polar33892256
Hydantoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC(=O)NC1=O1681.3Standard non polar33892256
Hydantoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC(=O)NC1=O2748.2Standard polar33892256
Hydantoin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)CNC1=O1644.6Semi standard non polar33892256
Hydantoin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)CNC1=O1643.5Standard non polar33892256
Hydantoin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)CNC1=O2623.1Standard polar33892256
Hydantoin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC(=O)N([Si](C)(C)C(C)(C)C)C1=O1852.9Semi standard non polar33892256
Hydantoin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC(=O)N([Si](C)(C)C(C)(C)C)C1=O1935.8Standard non polar33892256
Hydantoin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CC(=O)N([Si](C)(C)C(C)(C)C)C1=O1951.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydantoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zor-9200000000-00dd275be69e09ff78312021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydantoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 10V, Positive-QTOFsplash10-0udi-0900000000-d5fea3cc3a38fd5026922015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 20V, Positive-QTOFsplash10-0udi-3900000000-fcab5c6b0722c56015952015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 40V, Positive-QTOFsplash10-053r-9000000000-9be606f50cf484530f232015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 10V, Negative-QTOFsplash10-0002-9000000000-79f2feeafcde1e42f7aa2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 20V, Negative-QTOFsplash10-0006-9000000000-c6cb46642e3e5214a51c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 40V, Negative-QTOFsplash10-054o-9000000000-34a53a0f58ee15dcb29b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 10V, Positive-QTOFsplash10-0udi-2900000000-542377286d0f25dd0d9d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 20V, Positive-QTOFsplash10-0pi3-9200000000-72fe0474d06c3c95c4be2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 40V, Positive-QTOFsplash10-0006-9000000000-5bf44c25d5232c7b55992021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 10V, Negative-QTOFsplash10-0007-9000000000-3451fd1c05a1811950232021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 20V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004274
KNApSAcK IDC00038953
Chemspider ID9612
KEGG Compound IDC05146
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydantoin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID27612
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

General function:
Not Available
Specific function:
DNA glycosylase which prefers single-stranded DNA (ssDNA), or partially ssDNA structures such as bubble and fork structures, to double-stranded DNA (dsDNA) (PubMed:20185759, PubMed:22065741, PubMed:22569481, PubMed:22959434, PubMed:23305905, PubMed:23313161). Mediates interstrand cross-link repair in response to replication stress: acts by mediating DNA glycosylase activity, cleaving one of the two N-glycosyl bonds comprising the interstrand cross-link, which avoids the formation of a double-strand break but generates an abasic site that is bypassed by translesion synthesis polymerases (By similarity). In vitro, displays strong glycosylase activity towards the hydantoin lesions spiroiminodihydantoin (Sp) and guanidinohydantoin (Gh) in both ssDNA and dsDNA; also recognizes FapyA, FapyG, 5-OHU, 5-OHC, 5-OHMH, Tg and 8-oxoA lesions in ssDNA (PubMed:20185759, PubMed:22065741, PubMed:22569481, PubMed:22959434, PubMed:23305905, PubMed:23313161). No activity on 8-oxoG detected (PubMed:20185759, PubMed:22065741, PubMed:22569481, PubMed:22959434, PubMed:23305905, PubMed:23313161). Also shows weak DNA-(apurinic or apyrimidinic site) lyase activity (PubMed:20185759, PubMed:22065741, PubMed:22569481, PubMed:22959434, PubMed:23305905, PubMed:23313161). In vivo, appears to be the primary enzyme involved in removing Sp and Gh from ssDNA in neonatal tissues (PubMed:20185759, PubMed:22065741, PubMed:22569481, PubMed:22959434, PubMed:23305905, PubMed:23313161).
Gene Name:
NEIL3
Uniprot ID:
Q8K203
Molecular weight:
67415.815
General function:
Not Available
Specific function:
Catalyzes the conversion of allantoin (5-ureidohydantoin) to allantoic acid by hydrolytic cleavage of the five-member hydantoin ring.
Gene Name:
ALLB
Uniprot ID:
A1A8H7
Molecular weight:
49587.21
General function:
Not Available
Specific function:
Catalyzes the conversion of allantoin (5-ureidohydantoin) to allantoic acid by hydrolytic cleavage of the five-member hydantoin ring.
Gene Name:
ALLB
Uniprot ID:
Q5PCG0
Molecular weight:
49886.51
General function:
Not Available
Specific function:
DNA glycosylase which prefers single-stranded DNA (ssDNA), or partially ssDNA structures such as bubble and fork structures, to double-stranded DNA (dsDNA) (PubMed:12433996, PubMed:19170771, PubMed:22569481, PubMed:23755964). Mediates interstrand cross-link repair in response to replication stress: acts by mediating DNA glycosylase activity, cleaving one of the two N-glycosyl bonds comprising the interstrand cross-link, which avoids the formation of a double-strand break but generates an abasic site that is bypassed by translesion synthesis polymerases (By similarity). In vitro, displays strong glycosylase activity towards the hydantoin lesions spiroiminodihydantoin (Sp) and guanidinohydantoin (Gh) in both ssDNA and dsDNA; also recognizes FapyA, FapyG, 5-OHU, 5-OHC, 5-OHMH, Tg and 8-oxoA lesions in ssDNA (PubMed:12433996, PubMed:19170771, PubMed:22569481, PubMed:23755964). No activity on 8-oxoG detected (PubMed:12433996, PubMed:19170771, PubMed:22569481, PubMed:23755964). Also shows weak DNA-(apurinic or apyrimidinic site) lyase activity (PubMed:12433996, PubMed:19170771, PubMed:22569481, PubMed:23755964). In vivo, appears to be the primary enzyme involved in removing Sp and Gh from ssDNA in neonatal tissues (PubMed:12433996, PubMed:19170771, PubMed:22569481, PubMed:23755964).
Gene Name:
NEIL3
Uniprot ID:
Q8TAT5
Molecular weight:
67768.55