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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2020-02-26 21:24:00 UTC
HMDB IDHMDB0002271
Secondary Accession Numbers
  • HMDB02271
Metabolite Identification
Common NameImidazolepropionic acid
DescriptionImidazolepropionic acid, also known as deaminohistidine or 4-imidazolylpropionate, 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. Imidazolepropionic acid is a very strong basic compound (based on its pKa). Imidazolepropionic acid is a product of histidine metabolism which may involve oxidation or transamination. This compound is found in the urine of rats loaded with histidine (PMID: 6021220 ).
Structure
Data?1582752240
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
DihydrourocanateHMDB
3-(1H-Imidazol-4-yl)-propionateHMDB
3-(1H-Imidazol-4-yl)-propionic acidHMDB
5-ImidazolepropionateHMDB
5-Imidazolepropionic acidHMDB
Deamino-histidineHMDB
UROHMDB
Imidazole propionateHMDB
1H-Imidazole-4(5)-propanoateGenerator
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 Weight140.1399
Monoisotopic Molecular Weight140.05857751
IUPAC Name3-(1H-imidazol-5-yl)propanoic acid
Traditional Name5-imidazolepropionic acid
CAS Registry Number1074-59-5
SMILES
OC(=O)CCC1=CNC=N1
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point206 - 208 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility43.9 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    SalivaDetected but not Quantified Adult (>18 years old)MaleSupragingival Plaque details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
    Supragingival Plaque
    1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB012461
    KNApSAcK IDNot Available
    Chemspider ID63798
    KEGG Compound IDC20522
    BioCyc IDCPD-15171
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6585
    PubChem Compound70630
    PDB IDNot Available
    ChEBI ID73087
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceAkabori, 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.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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. [PubMed:6021220 ]
    2. 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. [PubMed:6136484 ]
    3. 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. [PubMed:13987921 ]
    4. 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. [PubMed:32033212 ]