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Showing NP-Card for N-Methylhydantoin (NP0000292)

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Record Information
Version2.0
Created at2006-08-13 02:29:33 UTC
Updated at2023-04-28 22:30:38 UTC
NP-MRD IDNP0000292
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Methylhydantoin
DescriptionN-methylhydantoin is a imidazolidine-2,4-dione that is the N-methyl-derivative of hydantoin. It has a role as a bacterial metabolite. It derives from a hydantoin. N-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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000292 (N-Methylhydantoin)


  Mrv1652305271900232D          

  8  8  0  0  0  0            999 V2000
   24.4142  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5099  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3746  -14.7269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9621  -15.9965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8596  -14.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5495  -14.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6295  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2946  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  8  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000292 (N-Methylhydantoin)

HMDB0003646
     RDKit          3D
N-Methylhydantoin
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9188    0.2379   -0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.1783    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152   -0.9700    0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -0.8488   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458   -1.7687   -0.4183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883    0.5411   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5025    1.1714   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    2.3979   -0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    1.0001   -0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2407   -0.7508   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.4931    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3277   -0.7825    1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026   -1.9181    0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    1.0191   -0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
Download

3D SDF for NP0000292 (N-Methylhydantoin)


  Mrv1652305271900232D          

  8  8  0  0  0  0            999 V2000
   24.4142  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5099  -15.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3746  -14.7269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9621  -15.9965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8596  -14.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5495  -14.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6295  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2946  -15.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  8  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000292

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
RHYBFKMFHLPQPH-UHFFFAOYSA-N

> <FORMULA>
C4H6N2O2

> <MOLECULAR_WEIGHT>
114.1026

> <EXACT_MASS>
114.042927446

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.248660447524124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methylimidazolidine-2,4-dione

> <ALOGPS_LOGP>
-1.20

> <JCHEM_LOGP>
-1.2265444019999998

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.109753519841874

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.940479971810053

> <JCHEM_PKA_STRONGEST_BASIC>
-8.478788567664584

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
25.9428

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methylhydantoin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000292 (N-Methylhydantoin)

HMDB0003646
     RDKit          3D
N-Methylhydantoin
 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.9188    0.2379   -0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.1783    0.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152   -0.9700    0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -0.8488   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458   -1.7687   -0.4183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883    0.5411   -0.2292 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5025    1.1714   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    2.3979   -0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    1.0001   -0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2407   -0.7508   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    0.4931    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3277   -0.7825    1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3026   -1.9181    0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088    1.0191   -0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
M  END
Download

PDB for NP0000292 (N-Methylhydantoin)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      45.573 -29.431   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      40.152 -29.431   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      43.633 -27.490   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      42.863 -29.860   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      44.538 -26.244   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.092 -27.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      44.108 -28.955   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.617 -28.955   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    5    6    7                                                  
CONECT    4    7    8                                                       
CONECT    5    3                                                            
CONECT    6    3    8                                                       
CONECT    7    1    3    4                                                  
CONECT    8    2    4    6                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0000292 (N-Methylhydantoin)

COMPND    HMDB0003646
HETATM    1  C1  UNL     1      -1.919   0.238  -0.219  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.498   0.178   0.033  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.215  -0.970   0.568  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.535  -0.849  -0.063  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.346  -1.769  -0.418  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.788   0.541  -0.229  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.502   1.171  -0.166  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.229   2.398  -0.263  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.192   1.000  -0.969  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.241  -0.751  -0.635  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.501   0.493   0.702  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.328  -0.782   1.673  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.303  -1.918   0.357  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.709   1.019  -0.369  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    7
CONECT    3    4   12   13
CONECT    4    5    5    6
CONECT    6    7   14
CONECT    7    8    8
END
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SMILES for NP0000292 (N-Methylhydantoin)

CN1CC(=O)NC1=O
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INCHI for NP0000292 (N-Methylhydantoin)

InChI=1S/C4H6N2O2/c1-6-2-3(7)5-4(6)8/h2H2,1H3,(H,5,7,8)
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View in JSmol
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
N-MethylhydantoinMeSH
Chemical FormulaC4H6N2O2
Average Mass114.1026 Da
Monoisotopic Mass114.04293 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2023-04-28View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pogostemon cablinLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazolines. These are organic compounds containing an imidazoline ring, which is an unsaturated ring (derived from imidazole) with two nitrogen atoms at positions 1 and 3 respectively, and containing only one CN double bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolines
Sub ClassImidazolines
Direct ParentImidazolines
Alternative Parents
Substituents
  • 3-imidazoline
  • Carbonic acid derivative
  • Azacycle
  • 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
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)8.94ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003646
DrugBank IDNot Available
Phenol Explorer Compound 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
Good Scents IDNot Available
References
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 ]
  5. Lee S, Ku JY, Kang BJ, Kim KH, Ha HK, Kim S: A Unique Urinary Metabolic Feature for the Determination of Bladder Cancer, Prostate Cancer, and Renal Cell Carcinoma. Metabolites. 2021 Sep 2;11(9). pii: metabo11090591. doi: 10.3390/metabo11090591. [PubMed:34564407 ]