Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:17:42 UTC
Update Date2024-04-30 20:33:15 UTC
Metabolite IDMMDBc0047943
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
Synonyms
ValueSource
1H-Imidazole-4-acetaldehydeChEBI
Imidazole acetaldehydeChEBI
1H-Imidazole-5-acetaldehydeHMDB
4-ImidazolylacetaldehydeHMDB
Imidazole-4(or 5)-acetaldehydeHMDB
Molecular FormulaC5H6N2O
Average Mass110.1139
Monoisotopic Mass110.048012824
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