Human Metabolome Database Version 3.5

Showing metabocard for Imidazole-4-acetaldehyde (HMDB03905)

Record Information
Version 3.5
Creation Date 2006-08-13 01:02:23 -0600
Update Date 2013-05-29 13:39:07 -0600
HMDB ID HMDB03905
Secondary Accession Numbers
  • HMDB06237
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 Link_out, 2957640 Link_out, 11536478 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1H-Imidazole-4-acetaldehyde
  2. 1H-Imidazole-5-acetaldehyde
  3. 4-Imidazolylacetaldehyde
  4. Imidazole acetaldehyde
  5. 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)
Substituents
  • Aldehyde
Direct Parent Imidazoles
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
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
Predicted Properties
Property Value Source
Water Solubility 229 g/L ALOGPS
LogP -0.28 ALOGPS
LogP -0.75 ChemAxon
LogS 0.32 ALOGPS
pKa (strongest acidic) 11.79 ChemAxon
pKa (strongest basic) 6.69 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 45.75 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 29.27 ChemAxon
Polarizability 10.58 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Histidine Metabolism SMP00044 map00340 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite 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 Link_out
KEGG Compound ID C05130 Link_out
BioCyc ID Not Available
BiGG ID 45184 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB03905 Link_out
Metagene Link HMDB03905 Link_out
METLIN ID Not Available
PubChem Compound 150841 Link_out
PDB ID Not Available
ChEBI ID 27398 Link_out
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
  1. Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase. Activity with aldehyde metabolites of monoamines, diamines, and polyamines. J Biol Chem. 1991 Jul 15;266(20):13011-8. Pubmed: 2071588 Link_out
  2. Shen C, Yang L, Miller SL, Oro J: Prebiotic synthesis of imidazole-4-acetaldehyde and histidine. Orig Life Evol Biosph. 1987;17(3-4):295-305. Pubmed: 2957640 Link_out
  3. Shen C, Yang L, Miller SL, Oro J: Prebiotic synthesis of histidine. J Mol Evol. 1990 Sep;31(3):167-74. Pubmed: 11536478 Link_out

Enzymes
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Ion details
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Ion details
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions: Not Available
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Ion details
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Ion details
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
Imidazole-4-acetaldehyde + NAD + Water unknown Imidazoleacetic acid + NADH + Hydrogen Ion details
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amiloride-sensitive amine oxidase [copper-containing]
Reactions:
Histamine + Water + Oxygen unknown Imidazole-4-acetaldehyde + Ammonia + Hydrogen peroxide details
Gene Name: ABP1
Uniprot ID: P19801 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA