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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:53 UTC
HMDB IDHMDB01525
Secondary Accession NumbersNone
Metabolite Identification
Common NameImidazole
DescriptionImidazole is a heterocyclic aromatic organic compound. It is further classified as an alkaloid. Imidazole refers to the parent compound C3H4N2, while imidazoles are a class of heterocycles with similar ring structure but varying substituents. This ring system is present in important biological building blocks such as histidine and histamine. Imidazole can act as a base and as a weak acid. Imidazole exists in two tautomeric forms with the hydrogen atom moving between the two nitrogens. Many drugs contain an imidazole ring, such as antifungal drugs and nitroimidazole. Imidazole is a 5 membered planar ring which is soluble in water and polar solvents. Imidazole is a base and an excellent nucleophile. It reacts at the NH nitrogen, attacking alkylating and acylating compounds. It is not particularly susceptible to electrophilic attacks at the carbon atoms, and most of these reactions are substitutions that keep the aromaticity intact. One can see from the resonance structure that the carbon-2 is the carbon most likely to have a nucleophile attack it, but in general nucleophilic substitutions are difficult with imidazole. Imidazole is incorporated into many important biological molecules. The most obvious is the amino acid histidine, which has an imidazole side chain. histidine is present in many proteins and enzymes and plays a vital part in the structure and binding functions of hemoglobin.
Structure
Thumb
Synonyms
ValueSource
1,3-Diaza-2,4-cyclopentadieneChEBI
1,3-DiazoleChEBI
GlyoxalineChEBI
HimChEBI
IMDChEBI
ImidazolChEBI
ImidazoleChEBI
IminazoleChEBI
MiazoleChEBI
N,N'-1,2-ethenediylmethanimidamideChEBI
N,N'-vinyleneformamidineChEBI
pyrro[b]MonazoleChEBI
GlyoxalinHMDB
ImutexHMDB
pyrro(b)MonazoleHMDB
{Pyrro[b]monazole}HMDB
Chemical FormulaC3H4N2
Average Molecular Weight68.0773
Monoisotopic Molecular Weight68.037448138
IUPAC Name1H-imidazole
Traditional NameHim
CAS Registry Number288-32-4
SMILES
N1C=CN=C1
InChI Identifier
InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
InChI KeyInChIKey=RAXXELZNTBOGNW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as imidazoles. These 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
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.08HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility538.0 mg/mLALOGPS
logP-0.21ALOGPS
logP-0.15ChemAxon
logS0.9ALOGPS
pKa (Strongest Acidic)13.4ChemAxon
pKa (Strongest Basic)6.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.01 m3·mol-1ChemAxon
Polarizability6.56 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014l-9000000000-2ca95342014cfc85bb74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-7d24c7b22fb67b2a5b76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-f50f9a9c83174e9c149fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-014l-9000000000-e6b2b7faf77dcf80d593View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-9000000000-76b001eeacbb900271faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-9000000000-5398a23c5b95419a1e5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-ad715dac27bd6d79523dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-9dad13fc804c087084a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-36c1868da6ae549e0d51View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Adrenal Cortex
  • Adrenal Gland
  • Epidermis
  • Liver
  • Neuron
  • Placenta
  • Platelet
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified9.42 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03366
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012307
KNApSAcK IDNot Available
Chemspider ID773
KEGG Compound IDC01589
BioCyc IDIMIDAZOLE-RING
BiGG IDNot Available
Wikipedia LinkImidazole
NuGOwiki LinkHMDB01525
Metagene LinkHMDB01525
METLIN ID4190
PubChem Compound795
PDB ID1AKY
ChEBI ID16069
References
Synthesis ReferenceLu, Zhongmin; Liu, Xinzheng. Review of process for synthesis of imidazole. Huagong Shikan (1999), 13(2), 26-27.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bruynseels J, De Coster R, Van Rooy P, Wouters W, Coene MC, Snoeck E, Raeymaekers A, Freyne E, Sanz G, Vanden Bussche G, et al.: R 75251, a new inhibitor of steroid biosynthesis. Prostate. 1990;16(4):345-57. [2164659 ]
  2. Sheu JR, Hsiao G, Shen MY, Lin WY, Tzeng CR: The hyperaggregability of platelets from normal pregnancy is mediated through thromboxane A2 and cyclic AMP pathways. Clin Lab Haematol. 2002 Apr;24(2):121-9. [11985559 ]
  3. Lamberts SW, Bruining HA, Marzouk H, Zuiderwijk J, Uitterlinden P, Blijd JJ, Hackeng WH, De Jong FH: The new aromatase inhibitor CGS-16949A suppresses aldosterone and cortisol production by human adrenal cells in vitro. J Clin Endocrinol Metab. 1989 Oct;69(4):896-901. [2550511 ]
  4. Luft FC, Mann JF: New classes of antihypertensive drugs and new findings with established agents. Curr Opin Nephrol Hypertens. 1992 Oct;1(1):91-9. [1365836 ]
  5. Allolio B, Stuttmann R, Winkelmann W: Missing effect of etomidate on testosterone secretion in man. Klin Wochenschr. 1986 Jan 15;64(2):86-8. [3005757 ]
  6. Schraag S, Pawlik M, Mohl U, Bohm BO, Georgieff M: The role of ascorbic acid and xylitol in etomidate-induced adrenocortical suppression in humans. Eur J Anaesthesiol. 1996 Jul;13(4):346-51. [8842654 ]
  7. Cotovio J, Roguet R, Pion FX, Rougier A, Leclaire J: Effect of imidazole derivatives on cytochrome P-450 enzyme activities in a reconstructed human epidermis. Skin Pharmacol. 1996;9(4):242-9. [8896115 ]
  8. Kuhlkamp V, Schmid F, Ress KM, Kramer BK, Mayer F, Liebich HM, Risler T, Seipel L: Quantification of cibenzoline and its imidazole metabolite by high-performance liquid chromatography in human serum. J Chromatogr. 1990 Jun 8;528(1):267-73. [2384563 ]
  9. Santella RM, Yang XY, Hsieh LL, Young TL: Immunologic methods for the detection of carcinogen adducts in humans. Prog Clin Biol Res. 1990;340C:247-57. [2199982 ]
  10. Howden CW, Kenyon CJ, Beastall GH, Reid JL: Inhibition by omeprazole of adrenocortical response to ACTH: clinical studies and experiments on bovine adrenal cortex in vitro. Clin Sci (Lond). 1986 Jan;70(1):99-102. [3002707 ]
  11. Baynes J, Levine M: Urea-extractable protein from human epidermis. Biochim Biophys Acta. 1976 Jul 19;439(1):107-15. [952948 ]
  12. Shishu, Singla AK, Kaur IP: Inhibitory effect of dibenzoylmethane on mutagenicity of food-derived heterocyclic amine mutagens. Phytomedicine. 2003;10(6-7):575-82. [13678246 ]
  13. Caccuri AM, Ascenzi P, Lo Bello M, Federici G, Battistoni A, Mazzetti P, Ricci G: Are the steady state kinetics of glutathione transferase always dependent on the deprotonation of the bound glutathione? New insights in the kinetic mechanism of GST P 1-1. Biochem Biophys Res Commun. 1994 May 16;200(3):1428-34. [8185596 ]
  14. Vanden Bossche H, Marichal P, Gorrens J, Coene MC, Willemsens G, Bellens D, Roels I, Moereels H, Janssen PA: Biochemical approaches to selective antifungal activity. Focus on azole antifungals. Mycoses. 1989;32 Suppl 1:35-52. [2561184 ]
  15. Smith DP, Smith DG, Curtain CC, Boas JF, Pilbrow JR, Ciccotosto GD, Lau TL, Tew DJ, Perez K, Wade JD, Bush AI, Drew SC, Separovic F, Masters CL, Cappai R, Barnham KJ: Copper-mediated amyloid-beta toxicity is associated with an intermolecular histidine bridge. J Biol Chem. 2006 Jun 2;281(22):15145-54. Epub 2006 Apr 4. [16595673 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in binding
Specific function:
Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
Gene Name:
LTA4H
Uniprot ID:
P09960
Molecular weight:
69284.64
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General function:
Involved in protein kinase activity
Specific function:
May affect the structure or silencing of chromatin by phosphorylating HP1 gamma/CBX3. Isoform 2 promotes the G1/S transition of the cell cycle via up-regulation of CDK2 activity and phosphorylation of CDKN1B, resulting in enhanced nuclear export and proteasome-dependent degradation of CDKN1B. Isoform 2 also represses CDKN1B transcription by phosphorylating and inactivating the transcription factor FOXO3. Plays a role in signal transduction in blood cells. Contributes to both cell proliferation and survival and thus provides a selective advantage in tumorigenesis
Gene Name:
PIM1
Uniprot ID:
P11309
Molecular weight:
45411.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General function:
Involved in iron ion binding
Specific function:
Plays a role in apoptosis. Suppression of the anti- apoptotic members or activation of the pro-apoptotic members of the Bcl-2 family leads to altered mitochondrial membrane permeability resulting in release of cytochrome c into the cytosol. Binding of cytochrome c to Apaf-1 triggers the activation of caspase-9, which then accelerates apoptosis by activating other caspases
Gene Name:
CYCS
Uniprot ID:
P99999
Molecular weight:
11748.7
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in iron ion binding
Specific function:
Serves as a reserve supply of oxygen and facilitates the movement of oxygen within muscles
Gene Name:
MB
Uniprot ID:
P02144
Molecular weight:
17183.7
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:
Microtubule-associated protein involved in membrane protein-cytoskeleton interactions. It is thought to anchor the inhibitory glycine receptor (GLYR) to subsynaptic microtubules (By similarity). Catalyzes two steps in the biosynthesis of the molybdenum cofactor. In the first step, molybdopterin is adenylated. Subsequently, molybdate is inserted into adenylated molybdopterin and AMP is released.
Gene Name:
GPHN
Uniprot ID:
Q9NQX3
Molecular weight:
79747.635
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth. Plays a key role in hematopoiesis.
Gene Name:
AK2
Uniprot ID:
P54819
Molecular weight:
24648.125
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]