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Record Information
Version3.6
Creation Date2006-08-13 02:29:33 UTC
Update Date2016-02-11 01:06:24 UTC
HMDB IDHMDB03646
Secondary Accession NumbersNone
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
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 KeyInChIKey=RHYBFKMFHLPQPH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Ureide
  • Urea
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility265.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.94 m3·mol-1ChemAxon
Polarizability10.25 Å3ChemAxon
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
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
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 Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
NuGOwiki LinkHMDB03646
Metagene LinkHMDB03646
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. [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. [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. [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. [7294979 ]