You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:02:23 UTC
Update Date2020-02-26 21:24:50 UTC
HMDB IDHMDB0003905
Secondary Accession Numbers
  • HMDB0006237
  • HMDB03905
  • HMDB06237
Metabolite Identification
Common NameImidazole-4-acetaldehyde
DescriptionImidazole-4-acetaldehyde 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. Imidazole-4-acetaldehyde is a very strong basic compound (based on its pKa). Imidazole-4-acetaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, imidazole-4-acetaldehyde participates in a number of enzymatic reactions. In particular, imidazole-4-acetaldehyde can be converted into imidazoleacetic acid through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In addition, imidazole-4-acetaldehyde can be biosynthesized from histamine through its interaction with the enzyme amiloride-sensitive amine oxidase [copper-containing]. In humans, imidazole-4-acetaldehyde is involved in histidine metabolism. Outside of the human body, Imidazole-4-acetaldehyde has been detected, but not quantified in, several different foods, such as roselles, chinese cinnamons, sunflowers, half-highbush blueberries, and american cranberries. This could make imidazole-4-acetaldehyde a potential biomarker for the consumption of these foods. NAD-linked dehydrogenation of short chain aliphatic aldehydes has been found in virtually every organ of the mammalian body. Aldehyde dehydrogenase (EC1.2.1.3) is the only enzyme in the human liver capable of catalyzing dehydrogenation of aldehydes arising via monoamine, diamine, and plasma amine oxidases. Imidazole-4-acetaldehyde is a good substrate for all aldehyde dehydrogenase isozymes. Experimentally, the prebiotic formation of histidine has been accomplished by the reaction of erythrose with formamidine followed by a Strecker synthesis. Imidazole-4-acetaldehyde could have been converted to histidine on the primitive earth by a Strecker synthesis, and several prebiotic reactions could convert imidazole-4-glycol and imidazole-4-ethanol to imidazole-4-acetaldehyde. Imidazole-4-acetaldehyde is a naturally occurring aldehyde metabolite of histamine formed by the action of histaminase (E.C. 1.4.3.6), and can be synthesized by oxidation of histidine.
Structure
Data?1582752290
Synonyms
ValueSource
1H-Imidazole-4-acetaldehydeChEBI
Imidazole acetaldehydeChEBI
1H-Imidazole-5-acetaldehydeHMDB
4-ImidazolylacetaldehydeHMDB
Imidazole-4(or 5)-acetaldehydeHMDB
Chemical FormulaC5H6N2O
Average Molecular Weight110.1139
Monoisotopic Molecular Weight110.048012824
IUPAC Name2-(1H-imidazol-5-yl)acetaldehyde
Traditional Name1H-imidazole-5-acetaldehyde
CAS Registry Number645-14-7
SMILES
O=CCC1=CN=CN1
InChI Identifier
InChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7)
InChI KeyMQSRGWNVEZRLDK-UHFFFAOYSA-N
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
  • Alpha-hydrogen aldehyde
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.388Not Available
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
logP-0.28ALOGPS
logP-0.75ChemAxon
logS0.32ALOGPS
pKa (Strongest Acidic)11.79ChemAxon
pKa (Strongest Basic)6.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.27 m³·mol⁻¹ChemAxon
Polarizability10.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-1efd54ea7ec2b730f547Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-36122ec0895589b0d0bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9600000000-97998f328d9888613811Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9000000000-b240031657ec8c00b5b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-80a13fb75d777746ebc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-7900000000-2474bf70fe2a0a6443beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-675428a404b9d1b09c69Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030915
KNApSAcK IDNot Available
Chemspider ID132948
KEGG Compound IDC05130
BioCyc IDNot Available
BiGG ID45184
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150841
PDB IDNot Available
ChEBI ID27398
Food Biomarker OntologyNot Available
VMH IDIM4ACT
References
Synthesis ReferenceShen, Chun; Yang, Lily; Miller, Stanley L.; Oro, J. Prebiotic synthesis of imidazole-4-acetaldehyde and histidine. Origins of Life and Evolution of the Biosphere (1987), 17(3-4), 295-305.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase. Activity with aldehyde metabolites of monoamines, diamines, and polyamines. J Biol Chem. 1991 Jul 15;266(20):13011-8. [PubMed:2071588 ]
  2. Shen C, Yang L, Miller SL, Oro J: Prebiotic synthesis of imidazole-4-acetaldehyde and histidine. Orig Life Evol Biosph. 1987;17(3-4):295-305. [PubMed:2957640 ]
  3. Shen C, Yang L, Miller SL, Oro J: Prebiotic synthesis of histidine. J Mol Evol. 1990 Sep;31(3):167-74. [PubMed:11536478 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Imidazole-4-acetaldehyde + NAD + Water → Imidazoleacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Reactions
Histamine + Water + Oxygen → Imidazole-4-acetaldehyde + Ammonia + Hydrogen peroxidedetails