Showing metabocard for Imidazole-4-acetaldehyde (BMDB0003905)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:33 UTC
Update Date2020-05-21 16:28:38 UTC
BMDB IDBMDB0003905
Secondary Accession Numbers
  • BMDB03905
Metabolite Identification
Common NameImidazole-4-acetaldehyde
DescriptionImidazole-4-acetaldehyde belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Imidazole-4-acetaldehyde is possibly soluble (in water) and a very strong basic compound (based on its pKa). Imidazole-4-acetaldehyde exists in all living organisms, ranging from bacteria to humans. Imidazole-4-acetaldehyde participates in a number of enzymatic reactions, within cattle. In particular, Imidazole-4-acetaldehyde can be converted into imidazoleacetic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. In addition, Imidazole-4-acetaldehyde can be biosynthesized from histamine; which is catalyzed by the enzyme amiloride-sensitive amine oxidase [copper-containing]. In cattle, imidazole-4-acetaldehyde is involved in the metabolic pathway called the histidine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1H-Imidazole-4-acetaldehydeChEBI
Imidazole acetaldehydeChEBI
1H-Imidazole-5-acetaldehydeHMDB
4-ImidazolylacetaldehydeHMDB
Imidazole-4(or 5)-acetaldehydeHMDB
Chemical FormulaC5H6N2O
Average Molecular Weight110.1139
Monoisotopic Molecular Weight110.048012824
IUPAC Name2-(1H-imidazol-5-yl)acetaldehyde
Traditional Name1H-imidazole-5-acetaldehyde
CAS Registry Number645-14-7
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 KeyMQSRGWNVEZRLDK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazoles
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Imidazole
  • Alpha-hydrogen aldehyde
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.388Not Available
Predicted Properties
PropertyValueSource
logP-0.28ALOGPS
logP-0.75ChemAxon
logS0.32ALOGPS
pKa (Strongest Acidic)11.79ChemAxon
pKa (Strongest Basic)6.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.27 m³·mol⁻¹ChemAxon
Polarizability10.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-1efd54ea7ec2b730f547View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-36122ec0895589b0d0bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9600000000-97998f328d9888613811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9000000000-b240031657ec8c00b5b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-80a13fb75d777746ebc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-7900000000-2474bf70fe2a0a6443beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-675428a404b9d1b09c69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-7900000000-c4f61368cc3619bb7773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9200000000-9e8c3dcfaaa09901cae9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9000000000-6a5e80237e5580be2b3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5900000000-ebd2d5c38315d4194499View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-9000000000-8c7dbf64d5cb9a0b87c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-ff96dfd23fb87b7cdc02View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003905
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030915
KNApSAcK IDNot Available
Chemspider ID132948
KEGG Compound IDC05130
BioCyc IDNot Available
BiGG ID45184
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150841
PDB IDNot Available
ChEBI ID27398
References
Synthesis ReferenceShen, 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 ReferencesNot Available

Enzymes

Enzyme Details
1. Membrane primary amine oxidase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity (By similarity).
Gene Name:
AOC3
Uniprot ID:
Q9TTK6
Molecular weight:
84500.0
Reactions
Histamine + Water + Oxygen → Imidazole-4-acetaldehyde + Ammonia + Hydrogen peroxidedetails