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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:46:28 UTC
HMDB IDHMDB0001014
Secondary Accession Numbers
  • HMDB01014
Metabolite Identification
Common Name4-Imidazolone-5-propionic acid
Description4-Imidazolone-5-propionic acid, also known as 4-imidazolone-5-propanoate, 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. An imidazol-4-one having a 2-carboxyethyl substituent at the 5-position. 4-Imidazolone-5-propionic acid is a strong basic compound (based on its pKa). 4-Imidazolone-5-propionic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 4-imidazolone-5-propionic acid participates in a number of enzymatic reactions. In particular, 4-imidazolone-5-propionic acid can be converted into urocanic acid through its interaction with the enzyme urocanate hydratase. In addition, 4-imidazolone-5-propionic acid can be converted into formiminoglutamic acid through the action of the enzyme probable imidazolonepropionase. In humans, 4-imidazolone-5-propionic acid is involved in histidine metabolism.
Structure
Data?1582752171
Synonyms
ValueSource
4,5-Dihydro-4-oxo-5-imidazolepropanoateChEBI
4,5-Dihydro-5-oxo-1H-imidazole-4-propanoic acidChEBI
4-Imidazolone-5-propanoateChEBI
Imidazol-4-one-5-propionic acidChEBI
4,5-Dihydro-4-oxo-5-imidazolepropanoic acidGenerator
4,5-Dihydro-5-oxo-1H-imidazole-4-propanoateGenerator
4-Imidazolone-5-propanoic acidGenerator
Imidazol-4-one-5-propionateGenerator
4-Imidazolone-5-propionateGenerator
(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoateHMDB
(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acidHMDB
3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoateHMDB
3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoic acidHMDB
3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoateHMDB
3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acidHMDB
Imidazolone propionateHMDB
Imidazolone propionic acidHMDB
ImidazolonepropanoateHMDB
Imidazolonepropanoic acidHMDB
Chemical FormulaC6H8N2O3
Average Molecular Weight156.1393
Monoisotopic Molecular Weight156.053492132
IUPAC Name3-(5-oxo-4,5-dihydro-1H-imidazol-4-yl)propanoic acid
Traditional Name3-(5-oxo-1,4-dihydroimidazol-4-yl)propanoic acid
CAS Registry Number17340-16-8
SMILES
OC(=O)CCC1N=CNC1=O
InChI Identifier
InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)
InChI KeyHEXMLHKQVUFYME-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
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP-1.1ALOGPS
logP-2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)4.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.22 m³·mol⁻¹ChemAxon
Polarizability14.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.27831661259
DarkChem[M+H]+134.27831661259
DarkChem[M-H]-129.55831661259
DarkChem[M-H]-129.55831661259
AllCCS[M+H]+133.80732859911
AllCCS[M-H]-128.932859911
DeepCCS[M+H]+123.17430932474
DeepCCS[M-H]-119.45530932474
DeepCCS[M-2H]-156.29630932474
DeepCCS[M+Na]+131.73330932474
AllCCS[M+H]+133.832859911
AllCCS[M+H-H2O]+129.532859911
AllCCS[M+NH4]+137.932859911
AllCCS[M+Na]+139.032859911
AllCCS[M-H]-128.932859911
AllCCS[M+Na-2H]-130.232859911
AllCCS[M+HCOO]-131.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Imidazolone-5-propionic acidOC(=O)CCC1N=CNC1=O2666.1Standard polar33892256
4-Imidazolone-5-propionic acidOC(=O)CCC1N=CNC1=O1511.2Standard non polar33892256
4-Imidazolone-5-propionic acidOC(=O)CCC1N=CNC1=O1710.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Imidazolone-5-propionic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CNC1=O1747.7Semi standard non polar33892256
4-Imidazolone-5-propionic acid,1TMS,isomer #2C[Si](C)(C)N1C=NC(CCC(=O)O)C1=O1781.1Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C)C1=O1826.2Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C)C1=O1837.5Standard non polar33892256
4-Imidazolone-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C)C1=O2768.3Standard polar33892256
4-Imidazolone-5-propionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CNC1=O1972.9Semi standard non polar33892256
4-Imidazolone-5-propionic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC(CCC(=O)O)C1=O2037.8Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C(C)(C)C)C1=O2318.4Semi standard non polar33892256
4-Imidazolone-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C(C)(C)C)C1=O2259.0Standard non polar33892256
4-Imidazolone-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1N=CN([Si](C)(C)C(C)(C)C)C1=O2935.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Imidazolone-5-propionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-9500000000-a11c5ca5f02078a53fc72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Imidazolone-5-propionic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8920000000-fed80cbe61ee26d1486a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Imidazolone-5-propionic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Positive-QTOFsplash10-000i-0900000000-36ccc12772d3e7b3bc012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Positive-QTOFsplash10-01p9-0900000000-8c7ad9614b1acbee7f962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Positive-QTOFsplash10-0f6x-9000000000-0561b28120ae734b99cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-d24b3a3769f74c7e18582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Negative-QTOFsplash10-0a4u-8900000000-98a3f029124c94f1e6b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Negative-QTOFsplash10-0006-9100000000-c75d14d5396894fff6f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-c39bbd8fcbd13dc72dd12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Negative-QTOFsplash10-08gl-8900000000-9ecbb63abc1319562a122021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Negative-QTOFsplash10-000x-9000000000-50c3ee9255335f634b302021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 10V, Positive-QTOFsplash10-0bt9-0900000000-75e80efea901b323015e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 20V, Positive-QTOFsplash10-03di-6900000000-a2d551ead7379a1c56b72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Imidazolone-5-propionic acid 40V, Positive-QTOFsplash10-0006-9100000000-d2613558e32279e944b32021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022371
KNApSAcK IDNot Available
Chemspider ID125
KEGG Compound IDC03680
BioCyc IDNot Available
BiGG ID42318
Wikipedia LinkImidazol-4-one-5-propionic acid
METLIN ID319
PubChem Compound128
PDB IDNot Available
ChEBI ID27384
Food Biomarker OntologyNot Available
VMH ID4IZP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niederwieser A, Matasovic A, Steinmann B, Baerlocher K, Kempken B: Hydantoin-5-propionic aciduria in folic acid nondependent formiminoglutamic aciduria observed in two siblings. Pediatr Res. 1976 Apr;10(4):215-9. [PubMed:1272625 ]

Enzymes

General function:
Involved in urocanate hydratase activity
Specific function:
Not Available
Gene Name:
UROC1
Uniprot ID:
Q96N76
Molecular weight:
80911.275
Reactions
4-Imidazolone-5-propionic acid → Urocanic acid + Waterdetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:
Not Available
Gene Name:
AMDHD1
Uniprot ID:
Q96NU7
Molecular weight:
46742.505
Reactions
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic acid + Hydrogen Iondetails
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic aciddetails