Imidazole-4-acetaldehyde (BioCAD00000012366)
{$topic}
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
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).
DBLinks
- CAS Registry Number: 645-14-7
- PubChem CID: 150841
- ChEBI: 27398
- HMDB: HMDB0003905
- LipidMaps:
- KEGG: C05130
- BioCyc: IMIDAZOLE_ACETALDEHYDE
- NCBI MeSH: 1H-imidazole-4-acetaldehyde
- Wikipedia: Imidazole-4-acetaldehyde
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
- WishartLab ClassyFire: [Imidazoles] Imidazoles
- RefMet: [Imidazole alkaloids] Imidazole alkaloids
- ChEBI: [CHEBI:27398] imidazole-4-acetaldehyde
- Coconut NaturalProduct: [Imidazole alkaloids] Imidazole alkaloids
| 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 |
Taxonomy Source
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 |