You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 02:29:33 UTC
Update Date2017-12-07 01:52:38 UTC
HMDB IDHMDB0003646
Secondary Accession Numbers
  • HMDB03646
Metabolite Identification
Common NameN-Methylhydantoin
DescriptionN-Methylhydantoin is a small molecular weight polar substance, the product of degradation of creatinine by bacteria (hydrolyzed by creatinine iminohydrolase, EC 3.5.4.21 to ammonia and N-methylhydantoin). In mammals, the metabolism of 1-methylhydantoin occurs via 5-hydroxy-1-methylhydantoin. In a reported human case, 1-Methylhydantoin was found as an unexpected metabolite of the intelligence-affecting substance dupracetam. (PMID: 15533691 , 8287520 , 3196760 , 7294979 ).
Structure
Thumb
Synonyms
ValueSource
1-MethylhydantoinChEBI
Dioxy-creatinineChEBI
N-Methylimidazolidine-2,4-dioneChEBI
1-Methyl-2,4-imidazolidinedioneHMDB
1-Methyl-hydantoinHMDB
1-Methyldiazolidine-2,4-dioneHMDB
1-Methylimidazolidine-2,4-dioneHMDB
Chemical FormulaC4H6N2O2
Average Molecular Weight114.1026
Monoisotopic Molecular Weight114.042927446
IUPAC Name1-methylimidazolidine-2,4-dione
Traditional Name1-methylhydantoin
CAS Registry Number616-04-6
SMILES
CN1CC(=O)NC1=O
InChI Identifier
InChI=1S/C4H6N2O2/c1-6-2-3(7)5-4(6)8/h2H2,1H3,(H,5,7,8)
InChI KeyRHYBFKMFHLPQPH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as ureides. These are compounds containing an ureide group with the general structure R1-CO-NH-CO-N(R)2R3, formally derived by the acylation of urea. They can be subdivided in N-acyl or N,N'-diacyl ureas.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic carbonic acids and derivatives
Direct ParentUreides
Alternative Parents
Substituents
  • Ureide
  • 3-imidazoline
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.148Not Available
Predicted Properties
PropertyValueSource
Water Solubility265 g/LALOGPS
logP-1.2ALOGPS
logP-1.2ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-8.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.94 m³·mol⁻¹ChemAxon
Polarizability10.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0fk9-4900000000-a8b3d576e459e1de466aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0zmi-3940000000-da9839cad415e267478cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ox-9200000000-4251e6986ebaeb204747View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fk9-4900000000-a8b3d576e459e1de466aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zmi-3940000000-da9839cad415e267478cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uk9-0900000000-ffb0a5ce0c929cd0afa8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1930000000-872542cc1dbf141f07e4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-9100000000-71ac15ae9d6b7aad555bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-80d31223555bd671d61aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-2900000000-a87a626fea21c2278151View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-92124f86d92c2993b429View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-ee0c93975d2d700dd54fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-369f40286b64917044faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-80d31223555bd671d61aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-2900000000-a87a626fea21c2278151View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-92124f86d92c2993b429View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-ee0c93975d2d700dd54fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-369f40286b64917044faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-91e06dc366dc0cd2fa4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-f4ff3357c63ff0cb2478View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-7714b876ee3ab2dfe6e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-c501697bbbe71907f6c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-32a998020f78744cc9f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5970b741d3da9c093df2View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified8.947 +/- 7.774 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified4.9 (1.0-11.0) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified10.022 +/- 8.701 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023209
    KNApSAcK IDNot Available
    Chemspider ID62430
    KEGG Compound IDC02565
    BioCyc IDN-METHYLHYDANTOIN
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound69217
    PDB IDNot Available
    ChEBI ID16354
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Hollosi L, Kettrup A, Schramm KW: MMSPE-RP-HPLC method for the simultaneous determination of methimazole and selected metabolites in fish homogenates. J Pharm Biomed Anal. 2004 Nov 19;36(4):921-4. [PubMed:15533691 ]
    2. Fossati P, Ponti M, Passoni G, Tarenghi G, Melzi d'Eril GV, Prencipe L: A step forward in enzymatic measurement of creatinine. Clin Chem. 1994 Jan;40(1):130-7. [PubMed:8287520 ]
    3. Ienaga K, Nakamura K, Naka F, Goto T: The metabolism of 1-methylhydantoin via 5-hydroxy-1-methylhydantoin in mammals. Biochim Biophys Acta. 1988 Dec 15;967(3):441-3. [PubMed:3196760 ]
    4. Dell HD, Jacobi H, Kamp R, Kurz J, Wunsche C: [1-Methylhydantoin, an unexpected metabolite of the intelligence-affecting substance dupracetam (author's transl)]. Arch Pharm (Weinheim). 1981 Aug;314(8):697-702. [PubMed:7294979 ]