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Showing NP-Card for 4-methylimidazole (NP0264948)

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Record Information
Version2.0
Created at2022-09-08 08:45:11 UTC
Updated at2022-09-08 08:45:11 UTC
NP-MRD IDNP0264948
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-methylimidazole
Description4-Methylimidazole, also known as 4-me-I or 4MI, 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. 4-Methylimidazole is a very strong basic compound (based on its pKa). 4-methylimidazole is found in Sophora flavescens. 4-methylimidazole was first documented in 1978 (PMID: 24161). Imidazole substituted at position 4 by a methyl group (PMID: 16180012) (PMID: 17619857) (PMID: 2079523) (PMID: 2254202).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0264948 (4-methylimidazole)


  Mrv0541 05031422172D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
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3D MOL for NP0264948 (4-methylimidazole)

     RDKit          3D

 12 12  0  0  0  0  0  0  0  0999 V2000
    1.7005   -0.1688    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    0.0226    0.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    1.2480    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7024    1.0395    0.0369 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -0.2736   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7317   -0.8976   -0.1383 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -0.0322    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0241   -1.1302   -0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411    0.6293   -0.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    2.2222    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8686   -0.7401   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5523   -1.9192   -0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  5 11  1  0
  6 12  1  0
M  END
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3D SDF for NP0264948 (4-methylimidazole)


  Mrv0541 05031422172D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)

> <INCHI_KEY>
XLSZMDLNRCVEIJ-UHFFFAOYSA-N

> <FORMULA>
C4H6N2

> <MOLECULAR_WEIGHT>
82.1038

> <EXACT_MASS>
82.053098202

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
8.642319773100064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-1H-imidazole

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
0.054337116000000005

> <ALOGPS_LOGS>
0.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.776225731132378

> <JCHEM_PKA_STRONGEST_BASIC>
7.493325117110688

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
24.1625

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylimidazole

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0264948 (4-methylimidazole)

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PDB for NP0264948 (4-methylimidazole)
HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
CONECT    1    4                                                            
CONECT    2    4    5                                                       
CONECT    3    5    6                                                       
CONECT    4    1    2    6                                                  
CONECT    5    2    3                                                       
CONECT    6    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

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3D PDB for NP0264948 (4-methylimidazole)
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SMILES for NP0264948 (4-methylimidazole)
CC1=CN=CN1
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INCHI for NP0264948 (4-methylimidazole)
InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)
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Synonyms
ValueSource
4(5)-MethylimidazoleChEBI
4-Me-iChEBI
4-MEIChEBI
4MIChEBI
4-Methylimidazole oxalate (1:1)MeSH
4-Methylimidazole, ion(1-)MeSH
4-Methylimidazole hydrideMeSH
5-MethylimidazoleMeSH
Chemical FormulaC4H6N2
Average Mass82.1038 Da
Monoisotopic Mass82.05310 Da
IUPAC Name5-methyl-1H-imidazole
Traditional Name4-methylimidazole
CAS Registry NumberNot Available
SMILES
CC1=CN=CN1
InChI Identifier
InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)
InChI KeyXLSZMDLNRCVEIJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sophora flavescensLOTUS Database
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
  • Heteroaromatic compound
    • 

  • Imidazole
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.1ALOGPS
logP0.054ChemAxon
logS0.85ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)7.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.16 m³·mol⁻¹ChemAxon
Polarizability8.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB03385  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19262  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methylimidazole  
METLIN IDNot Available
PubChem Compound13195  
PDB IDNot Available
ChEBI ID40035  
Good Scents IDNot Available
References
General References
  1. Chan P, Mahler J, Travlos G, Nyska A, Wenk M: Induction of thyroid lesions in 14-week toxicity studies of 2 and 4-methylimidazole in Fischer 344/N rats and B6C3F1 mice. Arch Toxicol. 2006 Mar;80(3):169-80. doi: 10.1007/s00204-005-0018-4. Epub 2005  Sep 23. [PubMed:16180012  ] 
  2. Chan PC, Hill GD, Kissling GE, Nyska A: Toxicity and carcinogenicity studies of 4-methylimidazole in F344/N rats and B6C3F1 mice. Arch Toxicol. 2008 Jan;82(1):45-53. doi: 10.1007/s00204-007-0222-5. Epub 2007 Jul  10. [PubMed:17619857  ] 
  3. Karangwa E, Mitchell GE Jr, Tucker RE: High-performance liquid chromatographic determination of 4-methylimidazole in sheep plasma and in ammoniated tall fescue hay. J Chromatogr. 1990 Oct 26;532(1):105-13. doi: 10.1016/s0378-4347(00)83756-1. [PubMed:2079523  ] 
  4. Karangwa E, Mitchell GE Jr, Tucker RE: Pharmacokinetics of 4-methylimidazole in sheep. J Anim Sci. 1990 Oct;68(10):3277-84. doi: 10.2527/1990.68103277x. [PubMed:2254202  ] 
  5. Yong SH, Karel M: Reactions between peroxidizing lipids and histidyl residue analogues: enhancement of lipid oxidation and browning by 4-methylimidazole. Lipids. 1978 Jan;13(1):1-5. doi: 10.1007/BF02533359. [PubMed:24161  ] 
  6. LOTUS database [Link]