1H-Imidazole-4(5)-propanoic acid (CHEM028262)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:20:02 UTC
Update Date2016-11-09 01:18:39 UTC
Accession NumberCHEM028262
Identification
Common Name1H-Imidazole-4(5)-propanoic acid
ClassSmall Molecule
DescriptionA monocarboxylic acid that is propionic acid in which one of the hydrogens at position 3 has been replaced by an imidazol-4-yl group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1H-Imidazole-4-propanoic acidChEBI
3-(1H-Imidazol-4-yl)propionic acidChEBI
3-(Imidazol-4-yl)propanoic acidChEBI
3-(Imidazol-4-yl)propionic acidChEBI
4-Imidazolylpropanoic acidChEBI
4-Imidazolylpropionic acidChEBI
DeaminohistidineChEBI
Imidazolylpropionic acidChEBI
3-(1H-Imidazol-4-yl)propanoateKegg
1H-Imidazole-4-propanoateGenerator
3-(1H-Imidazol-4-yl)propionateGenerator
3-(Imidazol-4-yl)propanoateGenerator
3-(Imidazol-4-yl)propionateGenerator
4-ImidazolylpropanoateGenerator
4-ImidazolylpropionateGenerator
ImidazolylpropionateGenerator
3-(1H-Imidazol-4-yl)propanoic acidGenerator
ImidazolepropionateGenerator
3-(1H-Imidazol-4-yl)-propionateHMDB
3-(1H-Imidazol-4-yl)-propionic acidHMDB
5-ImidazolepropionateHMDB
5-Imidazolepropionic acidHMDB, MeSH
deamino-HistidineHMDB
UROHMDB
Imidazole propionateMeSH, HMDB
DihydrourocanateGenerator, HMDB
1H-Imidazole-4(5)-propanoateGenerator, HMDB
1H-Imidazole-4-propionic acidHMDB
3-(1H-4-Imidazolyl)propanoic acidHMDB
3-(1H-4-Imidazolyl)propionic acidHMDB
3-(4-Imidazolyl)propanoic acidHMDB
3-(4-Imidazolyl)propionic acidHMDB
3-(Imidazol-4(5)-yl)propanoic acidHMDB
3-(Imidazol-4(5)-yl)propionic acidHMDB
5-(2-Carboxyethyl) imidazoleHMDB
Dihydrourocanic acidHMDB
Dihydrourocanoic acidHMDB
Imidazole-4(5)-propanoic acidHMDB
Imidazole-4(5)-propionic acidHMDB
Imidazole-4-propanoic acidHMDB
Imidazole-4-propionic acidHMDB
Imidazolylpropanoic acidHMDB
beta-(5-Imidazolyl)propanoic acidHMDB
beta-(5-Imidazolyl)propionic acidHMDB
beta-Imidazolyl-4(5)-propanoic acidHMDB
beta-Imidazolyl-4(5)-propionic acidHMDB
β-(5-Imidazolyl)propanoic acidHMDB
β-(5-Imidazolyl)propionic acidHMDB
β-Imidazolyl-4(5)-propanoic acidHMDB
β-Imidazolyl-4(5)-propionic acidHMDB
Chemical FormulaC6H8N2O2
Average Molecular Mass140.140 g/mol
Monoisotopic Mass140.059 g/mol
CAS Registry Number1074-59-5
IUPAC Name3-(1H-imidazol-5-yl)propanoic acid
Traditional Name5-imidazolepropionic acid
SMILESOC(=O)CCC1=CN=CN1
InChI IdentifierInChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10)
InChI KeyZCKYOWGFRHAZIQ-UHFFFAOYSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility45.9 g/LALOGPS
logP-0.09ALOGPS
logP-1.1ChemAxon
logS-0.48ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.95 m³·mol⁻¹ChemAxon
Polarizability13.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-9200000000-8af7c94edf62d10d7905Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9200000000-466ffc1c8385b5811677Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 20V, Positivesplash10-0006-0900000000-593be5cf10aba06261f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-1900000000-f813e755bd0c33989b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-9700000000-fc60958d4ee5d49335caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-c8f93079184c6ee4b5d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-684a7e6823977a73c2b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-6900000000-3f4fc2398941bf5c7395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9100000000-49b8e29531a2099a80ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-9400000000-f2cb4a7574ec2ba4ce92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-9100000000-8e37d715ddc9ef376bf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-2ee2f80749be6e61f757Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-5900000000-bb071711eca6657a6d91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-4bbf16992517da7c64f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-fe8160b6c4b3de352e44Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002271
FooDB IDFDB012461
Phenol Explorer IDNot Available
KNApSAcK IDC00050820
BiGG IDNot Available
BioCyc IDCPD-15171
METLIN ID6585
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID63798
ChEBI ID73087
PubChem Compound ID70630
Kegg Compound IDC20522
YMDB IDNot Available
ECMDB IDM2MDB005794
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23078170
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2547218
3. Akabori, Shiro. Synthesis of imidazole derivatives from a-amino acids. I. A new synthesis of desaminohistidine and a contribution to the knowledge of the constitution of ergothioneine. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1933), 66B 151-8.
4. Akabori, Shiro. Synthesis of imidazole derivatives from a-amino acids. I. A new synthesis of desaminohistidine and a contribution to the knowledge of the constitution of ergothioneine. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1933), 66B 151-8.
5. Block WD, Westhoff MH, Steele BF: Histidine metabolism in the human adult: histidine blood tolerance, and the effect of continued free L-histidine ingestion on the concentration of imidazole compounds in blood and urine. J Nutr. 1967 Feb;91(2):189-94.
6. Antener I, Verwilghen AM, Van Geert C, Mauron J: Biochemical study of malnutrition. Part VI: Histidine and its metabolites. Int J Vitam Nutr Res. 1983;53(2):199-209.
7. SEN NP, McGEER PL, PAUL RM: Imidazolepropionic acid as a urinary metabolite of L-histidine. Biochem Biophys Res Commun. 1962 Oct 17;9:257-61.
8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.