Record Information
Version3.6
Creation Date2006-08-13 07:02:23 UTC
Update Date2013-05-29 19:39:07 UTC
HMDB IDHMDB03905
Secondary Accession Numbers
  • HMDB06237
Metabolite Identification
Common NameImidazole-4-acetaldehyde
DescriptionImidazole-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. Aldehyde dehydrogenase (EC 1.2.1.3) is the only enzyme in the human liver capable of catalyzing dehydrogenation of aldehydes arising via monoamine, diamine, and plasma amine oxidases. NAD-linked dehydrogenation of short chain aliphatic aldehydes has been found in virtually every organ of the mammalian body. 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. (PMID: 2071588 , 2957640 , 11536478 ).
Structure
Thumb
Synonyms
  1. 1H-Imidazole-4-acetaldehyde
  2. 1H-Imidazole-5-acetaldehyde
  3. 4-Imidazolylacetaldehyde
  4. Imidazole acetaldehyde
  5. Imidazole-4(or 5)-acetaldehyde
Chemical FormulaC5H6N2O
Average Molecular Weight110.1139
Monoisotopic Molecular Weight110.048012824
IUPAC Name2-(1H-imidazol-5-yl)acetaldehyde
Traditional IUPAC Name2-(3H-imidazol-4-yl)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
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassAzoles
Sub ClassImidazoles
Other Descriptors
  • a small molecule(Cyc)
  • imidazolylacetaldehyde(ChEBI)
Substituents
  • Aldehyde
Direct ParentImidazoles
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 area45.75ChemAxon
rotatable bond count2ChemAxon
refractivity29.27ChemAxon
polarizability10.58ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Histidine MetabolismSMP00044map00340
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023247
KNApSAcK IDNot Available
Chemspider ID132948
KEGG Compound IDC05130
BioCyc IDNot Available
BiGG ID45184
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03905
Metagene LinkHMDB03905
METLIN IDNot Available
PubChem Compound150841
PDB IDNot Available
ChEBI ID27398
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

Gene Name:
ALDH9A1
Uniprot ID:
P49189
Reactions
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Reactions
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH2
Uniprot ID:
P05091
Reactions
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Reactions
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Iondetails
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Reactions
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Iondetails
Gene Name:
ABP1
Uniprot ID:
P19801
Reactions
Histamine + Water + Oxygen unknown Imidazole-4-acetaldehyde + Ammonia + Hydrogen peroxidedetails