Record Information
Version2.0
Creation Date2012-05-31 14:00:10 -0600
Update Date2015-09-13 12:56:13 -0600
Secondary Accession Numbers
  • ECMDB03701
Identification
Name:Dimethylbenzimidazole
DescriptionDimethylbenzimidazole is an intermediate in Riboflavin metabolism.
Structure
Thumb
Synonyms:
  • 5,6-Dimethyl-1H-Benzimidazole
  • 5,6-Dimethylbenzimidazole
  • Dimedazole
  • Dimesol
  • Dimethylbenzimidazole
  • Dimezol (VAN)
  • DimezolDimedazol
  • DMB
Chemical Formula:C9H10N2
Weight:Average: 146.1891
Monoisotopic: 146.08439833
InChI Key:LJUQGASMPRMWIW-UHFFFAOYSA-N
InChI:InChI=1S/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11)
CAS number:582-60-5
IUPAC Name:5,6-dimethyl-1H-1,3-benzodiazole
Traditional IUPAC Name:5,6-dimethylbenzimidazole
SMILES:CC1=CC2=C(C=C1C)N=CN2
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Benzenoid
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:205.5 °C
Experimental Properties:
PropertyValueSource
LogP:1.854PhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.08 g/LALOGPS
logP1.88ALOGPS
logP2.29ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.73ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.05 m³·mol⁻¹ChemAxon
Polarizability16.47 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
adenosylcobalamin salvage from cobinamidePW001884 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000t-2900000000-cf01975179c82b56a747View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gb9-5790000000-e422b94d0cbe1bd0345eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000t-2900000000-cf01975179c82b56a747View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-5790000000-e422b94d0cbe1bd0345eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-1900000000-1cc9a65e6235151e4820View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-2590000000-7f1dc8fd34bdb99d58f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0900000000-94a00940d804552f77d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-d879a610883483e63326View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-1900000000-7810390c926bc0a2238aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-3900000000-0e438f149c15e3ba2238View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-1900000000-286b3359932c2c63dc23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-4900000000-4e9fbfe2a1943cc865e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0002-0900000000-4a48df4993767b5c4effView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0002-0900000000-93fb22bfd73cbaaecda9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-5f138fc55912e09c04f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000t-0900000000-0ac7250afc1fd38defe3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-941f6c90a92fad755dd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-4900000000-9778293bbdebe312995bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-0900000000-0581e550bdf15c825ed1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-4900000000-f22be5bed413f1b519e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-677d27a4db0421a0c22dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-3c2aee6880c85391a739View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-86d65abcc3c20eeaa9b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-25408408c64689b319eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-4cefb2993f948a46e8e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-92df1f58e19215585f6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a09abdb85c0cd0766165View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-2900000000-7ad608a4dad05614e995View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2f5826366923dad35341View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-685b19fc37ae77b7006bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-3900000000-1e116130bd866fe7fc71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-8ffc0ea3ec7f7e0434b8View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15890
HMDB IDHMDB03701
Pubchem Compound ID675
Kegg IDC03114
ChemSpider ID655
Wikipedia IDDimethylbenzimidazole
BioCyc IDDIMETHYLBENZIMIDAZOLE
EcoCyc IDDIMETHYLBENZIMIDAZOLE
Ligand ExpoDMD

Enzymes

General function:
Involved in nicotinate-nucleotide-dimethylbenzimidazole phosphoribosyltransferase activity
Specific function:
Catalyzes the synthesis of alpha-ribazole-5'-phosphate from nicotinate mononucleotide (NAMN) and 5,6- dimethylbenzimidazole (DMB)
Gene Name:
cobT
Uniprot ID:
P36562
Molecular weight:
36987
Reactions
Beta-nicotinate D-ribonucleotide + 5,6-dimethylbenzimidazole = nicotinate + alpha-ribazole 5'-phosphate.