Imidazole-4-acetaldehyde (BioCAD00000012366)

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Metabolite Card

Formula: C5H6N2O (110.048)
SMILES: O=CCC1=CN=CN1

Synonyms [en]

Imidazole-4-acetaldehyde; Imidazole acetaldehyde; 1H-Imidazole-4-acetaldehyde; 4-Imidazolylacetaldehyde; Imidazole-4(or 5)-acetaldehyde; B4S3Z68DDD

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Imidazole-4-acetaldehyde. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000012366). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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. 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).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 645-14-7
  • PubChem: 150841
  • ChEBI: ChEBI:27398
  • HMDB: HMDB0003905
  • HMDB: HMDB03905
  • KEGG: C05130
  • BioCyc: IMIDAZOLE_ACETALDEHYDE
  • NCBI MeSH: 1H-imidazole-4-acetaldehyde
  • Wikipedia: Imidazole-4-acetaldehyde
  • RefMet: RM0136245
  • Metlin: METLIN_58184
  • Coconut NaturalProduct: CNP0573000.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02150 1.4.3.22 1H-imidazole-4-ethanamine:oxygen oxidoreductase (deaminating) (copper-containing)
KEGG:R04065 1.2.1.3 imidazole acetaldehyde:NAD+ oxidoreductase
KEGG:R04874 C03277<=>C05130 + C00011
Rhea:RHEA:25626 1.4.3.22 histamine + O2 + H2O => imidazole-4-acetaldehyde + H2O2 + NH4+
Rhea:RHEA:25627 1.4.3.22 imidazole-4-acetaldehyde + H2O2 + NH4+ => histamine + O2 + H2O
Rhea:RHEA:25628 1.4.3.22 histamine + O2 + H2O <=> imidazole-4-acetaldehyde + H2O2 + NH4+
Rhea:RHEA:31060 imidazole-4-acetaldehyde + NAD+ + H2O => imidazole-4-acetate + NADH + 2 H+
Rhea:RHEA:31061 imidazole-4-acetate + NADH + 2 H+ => imidazole-4-acetaldehyde + NAD+ + H2O
Rhea:RHEA:31062 imidazole-4-acetaldehyde + NAD+ + H2O <=> imidazole-4-acetate + NADH + 2 H+
BioCyc:RXN-10089 1.2.1.3 imidazole acetaldehyde reductase
BioCyc:RXN-9600 1.4.3.22 HISTAMINE + WATER + OXYGEN-MOLECULE --> IMIDAZOLE_ACETALDEHYDE + AMMONIUM + HYDROGEN-PEROXIDE
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]
  2. Mus musculus [ncbi taxid: 10090]

Pathway Synthetic

pathway id name
BioCyc:MOUSE_PWY-6181 histamine degradation
BioCyc:META_PWY-6181 histamine degradation
BioCyc:HUMAN_PWY-6181 histamine degradation
Reactome:R-BTA-1430728 Metabolism
Reactome:R-BTA-211945 Phase I - Functionalization of compounds
Reactome:R-HSA-211859 Biological oxidations
Reactome:R-MMU-1430728 Metabolism
Reactome:R-MMU-211859 Biological oxidations
Reactome:R-RNO-211945 Phase I - Functionalization of compounds
Reactome:R-BTA-211859 Biological oxidations
Reactome:R-DRE-211945 Phase I - Functionalization of compounds
Reactome:R-RNO-211859 Biological oxidations
Reactome:R-XTR-211945 Phase I - Functionalization of compounds
Reactome:R-DRE-1430728 Metabolism
Reactome:R-GGA-1430728 Metabolism
Reactome:R-GGA-211859 Biological oxidations
Reactome:R-HSA-211945 Phase I - Functionalization of compounds
Reactome:R-MMU-211945 Phase I - Functionalization of compounds
Reactome:R-RNO-1430728 Metabolism
Reactome:R-XTR-1430728 Metabolism
View All Pathways