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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 03:39:40 UTC
Update Date2018-05-18 01:53:55 UTC
HMDB IDHMDB0003701
Secondary Accession Numbers
  • HMDB03701
Metabolite Identification
Common NameDimethylbenzimidazole
DescriptionDimethylbenzimidazole is an intermediate in Riboflavin metabolism. Dimethylbenzimidazole is the second to last step for the synthesis of alpha-Ribazole. It is converted from Riboflavin then it is converted to N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole via the enzyme nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase (EC 2.4.2.21).
Structure
Thumb
Synonyms
ValueSource
DimedazolChEBI
DimedazoleChEBI
DimesolChEBI
DimezolChEBI
5,6-Dimethyl-1H-benzimidazoleHMDB
5,6-DimethylbenzimidazoleHMDB
DimezolDimedazolHMDB
5,6-Dimethylbenzimidazole hydrochlorideMeSH
Chemical FormulaC9H10N2
Average Molecular Weight146.1891
Monoisotopic Molecular Weight146.08439833
IUPAC Name5,6-dimethyl-1H-1,3-benzodiazole
Traditional Name5,6-dimethylbenzimidazole
CAS Registry Number582-60-5
SMILES
CC1=CC2=C(C=C1C)N=CN2
InChI Identifier
InChI=1S/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11)
InChI KeyLJUQGASMPRMWIW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.854Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.08 g/LALOGPS
logP1.88ALOGPS
logP2.29ChemAxon
logS-1.8ALOGPS
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
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
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
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
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Prostate Tissue
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Prostate TissueDetected and Quantified0.5 (0.0-1.0) umol/g tissueAdult (>18 years old)Both
Prostate cancer
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023216
KNApSAcK IDNot Available
Chemspider ID655
KEGG Compound IDC03114
BioCyc IDDIMETHYLBENZIMIDAZOLE
BiGG IDNot Available
Wikipedia LinkDimethylbenzimidazole
METLIN IDNot Available
PubChem Compound675
PDB IDDMD
ChEBI ID15890
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]