| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-08-13 01:02:23 -0600 |
| Update Date |
2013-02-08 17:12:49 -0700 |
| HMDB ID |
HMDB03905 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
|---|
| Common Name |
Imidazole-4-acetaldehyde |
| Description |
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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1H-Imidazole-4-acetaldehyde
- 1H-Imidazole-5-acetaldehyde
- 4-Imidazolylacetaldehyde
- Imidazole acetaldehyde
- Imidazole-4(or 5)-acetaldehyde
|
| Chemical Formula |
C5H6N2O |
| Average Molecular Weight |
110.1139 |
| Monoisotopic Molecular Weight |
110.048012824 |
| IUPAC Name |
2-(1H-imidazol-5-yl)acetaldehyde |
| Traditional IUPAC Name |
2-(3H-imidazol-4-yl)acetaldehyde |
| CAS Registry Number |
645-14-7 |
| 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 Key |
MQSRGWNVEZRLDK-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteromonocyclic Compounds |
| Class |
Azoles |
| Sub Class |
Imidazoles |
| Other Descriptors |
- a small molecule(Cyc)
- imidazolylacetaldehyde(ChEBI)
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| Substituents |
|
| Direct Parent |
Imidazoles |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
Not Available |
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
0.388 |
Not Available |
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| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
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| Biological Properties |
|---|
| Cellular Locations |
Not Available
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| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023247 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
132948 |
| KEGG Compound ID |
C05130 |
| BioCyc ID |
Not Available |
| BiGG ID |
45184 |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB03905 |
| Metagene Link |
HMDB03905 |
| METLIN ID |
Not Available |
| PubChem Compound |
150841 |
| PDB ID |
Not Available |
| ChEBI ID |
27398 |
| References |
|---|
| Synthesis Reference |
Shen, 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 |
Not Available |
