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
Molecular FormulaC5H6N2O
Average Mass110.11390
Monoisotopic Mass110.04801
IUPAC Name2-(1H-imidazol-5-yl)acetaldehyde
Traditional Name2-(3h-imidazol-4-yl)acetaldehyde
CAS Registry Number645-14-7
SMILESO=CCc1c[nH]cn1
InChI IdentifierInChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7)
InChI KeyMQSRGWNVEZRLDK-UHFFFAOYSA-N
CHEBI IDCHEBI:27398
HMDB IDHMDB0003905
Pathways
NameSMPDB/PathBank
Histidine metabolism
Histidinemia
StateSolid
Water Solubility2.29e+02 g/l
logP-0.28
logS0.32
pKa (Strongest Acidic)11.79
pKa (Strongest Basic)6.69
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area45.75 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity29.27 m³·mol⁻¹
Polarizability10.58

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