Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2020-04-21 18:02:19 UTC
Primary IDFDB012464
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1H-Imidazole-4(5)-acetic acid
DescriptionImidazoleacetic acid, also known as 4(5)-imidazoleacetate or IAA, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Imidazoleacetic acid is a very strong basic compound (based on its pKa). Imidazoleacetic acid exists in all living organisms, ranging from bacteria to humans. Imidazoleacetic acid has been detected, but not quantified in, several different foods, such as small-leaf lindens, swiss chards, wild celeries, pak choy, and dandelions. This could make imidazoleacetic acid a potential biomarker for the consumption of these foods. Imidazoleacetic acid is a potentially toxic compound.
CAS Number645-65-8
Structure
Thumb
Synonyms
SynonymSource
1H-Imidazole-4-acetic acidChEBI
4(5)-ImidazoleacetateChEBI
4-ImidazoleacetateChEBI
Imidazole-4-acetateChEBI
1H-Imidazole-4-acetateGenerator
4(5)-Imidazoleacetic acidGenerator
4-Imidazoleacetic acidGenerator
Imidazole-4-acetic acidGenerator
ImidazoleacetateGenerator
1H-Imidazol-4-ylacetic acidHMDB
IAAHMDB
IMACHMDB
Imidazol-4-ylacetateHMDB
Imidazol-4-ylacetic acidHMDB
Imidazole acetateHMDB
Imidazolyl-4-acetic acidHMDB
IZCHMDB
Lopac-I-0375HMDB
Imidazole-4-acetic acid, sodium saltHMDB
Imidazole-4-acetic acid hydrochlorideHMDB
(1H-Imidazol-4-yl)-acetic acidbiospider
1H-Imidazole-4-acetic acid (9CI)biospider
Imidazole acetic acidmanual
Imidazole-4-acetic acid (8CI)biospider
Imidazoleacetic acidChEBI
Predicted Properties
PropertyValueSource
Water Solubility53.3 g/LALOGPS
logP-0.5ALOGPS
logP-1.4ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.2 m³·mol⁻¹ChemAxon
Polarizability11.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H6N2O2
IUPAC name2-(1H-imidazol-5-yl)acetic acid
InChI IdentifierInChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
InChI KeyPRJKNHOMHKJCEJ-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=CN=CN1
Average Molecular Weight126.1133
Monoisotopic Molecular Weight126.042927446
Classification
Description Belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Imidazolyl carboxylic acid derivative
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 47.62%; H 4.80%; N 22.21%; O 25.37%DFC
Melting PointMp 222° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS1H-Imidazole-4(5)-acetic acid, 1 TMS, GC-MS Spectrumsplash10-0f89-5900000000-420b0de40d13d8210bbcSpectrum
GC-MS1H-Imidazole-4(5)-acetic acid, 2 TMS, GC-MS Spectrumsplash10-0fc0-5970000000-86a11eed673e756aa38aSpectrum
GC-MS1H-Imidazole-4(5)-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-5900000000-420b0de40d13d8210bbcSpectrum
GC-MS1H-Imidazole-4(5)-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0fc0-5970000000-86a11eed673e756aa38aSpectrum
Predicted GC-MS1H-Imidazole-4(5)-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9200000000-3560ea9910e3fb51b173Spectrum
Predicted GC-MS1H-Imidazole-4(5)-acetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8900000000-05046aa1145002d7c5e8Spectrum
Predicted GC-MS1H-Imidazole-4(5)-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-9600000000-12712603bcc1f0bea126Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-fc527ff9b17df8a45f5dSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-f50438c3b380c53358cbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-0900000000-3e8a5824e3117a9ff630Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-9100000000-bd0eae5cae4e35af3bc9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-029fc71514700cdb7209Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-55f8440d265a11022fb9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-2f783a29f0103b0f7b59Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-9000000000-536179ad66be87ef6052Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-3e8a5824e3117a9ff630Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-bd0eae5cae4e35af3bc9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-029fc71514700cdb7209Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-55f8440d265a11022fb9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2f783a29f0103b0f7b59Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-004i-1900000000-2df669861c33e046ef52Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9000000000-9ab02097fca907a3b75fSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-9000000000-8c245e2f0f54c3db08d7Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9100000000-5976268b58ff0c9c054aSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9100000000-ffb1202ccd976a3c4ac6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1900000000-4b77cf695394035f5cb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-8900000000-3a84b22e5a91324c68a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc3-9000000000-c43447728a419e4b671aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-d826c494ed679b7cd08eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-9800000000-1d0c114437988870749dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kal-9100000000-802d3d5a745c25a2b664Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID86856
ChEMBL IDCHEMBL784
KEGG Compound IDC02835
Pubchem Compound ID96215
Pubchem Substance IDNot Available
ChEBI ID16974
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02024
CRC / DFC (Dictionary of Food Compounds) IDHHC19-P:HHC19-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID40666
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Histidine MetabolismSMP00044 map00340
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference