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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:31 UTC
HMDB IDHMDB0001212
Secondary Accession Numbers
  • HMDB01212
Metabolite Identification
Common NameHydantoin-5-propionic acid
DescriptionHydantoin-5-propionic acid, also known as hydantoin-propionate, belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4. Hydantoin-5-propionic acid exists in all living organisms, ranging from bacteria to humans. Hydantoin-5-propionic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make hydantoin-5-propionic acid a potential biomarker for the consumption of these foods. Hydantoin-5-propionic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Hydantoin-5-propionic acid.
Structure
Data?1676999731
Synonyms
ValueSource
Hydantoin-propionateKegg
Hydantoin-propionic acidGenerator
Hydantoin-5-propionateGenerator
1-(2,4-(3H,5H)Imidazoledione)propionic acidMeSH
Hydantoin-5-propionic acidGenerator
Chemical FormulaC6H8N2O4
Average Molecular Weight172.1387
Monoisotopic Molecular Weight172.048406754
IUPAC Name3-(2,5-dioxoimidazolidin-4-yl)propanoic acid
Traditional Namehydantoin-5-propionic acid
CAS Registry Number5624-26-0
SMILES
OC(=O)CCC1NC(=O)NC1=O
InChI Identifier
InChI=1S/C6H8N2O4/c9-4(10)2-1-3-5(11)8-6(12)7-3/h3H,1-2H2,(H,9,10)(H2,7,8,11,12)
InChI KeyVWFWNXQAMGDPGG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • 5-monosubstituted hydantoin
  • N-acyl urea
  • Ureide
  • Dicarboximide
  • Carbonic acid derivative
  • Urea
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility7.45 g/LALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.33 m³·mol⁻¹ChemAxon
Polarizability15.11 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]+139.42731661259
DarkChem[M-H]-131.20131661259
AllCCS[M+H]+136.88832859911
AllCCS[M-H]-132.5932859911
DeepCCS[M+H]+127.09230932474
DeepCCS[M-H]-123.25730932474
DeepCCS[M-2H]-160.08430932474
DeepCCS[M+Na]+135.66630932474
AllCCS[M+H]+136.932859911
AllCCS[M+H-H2O]+132.732859911
AllCCS[M+NH4]+140.832859911
AllCCS[M+Na]+141.932859911
AllCCS[M-H]-132.632859911
AllCCS[M+Na-2H]-133.632859911
AllCCS[M+HCOO]-134.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hydantoin-5-propionic acidOC(=O)CCC1NC(=O)NC1=O3027.3Standard polar33892256
Hydantoin-5-propionic acidOC(=O)CCC1NC(=O)NC1=O1763.7Standard non polar33892256
Hydantoin-5-propionic acidOC(=O)CCC1NC(=O)NC1=O1996.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydantoin-5-propionic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1NC(=O)NC1=O1915.8Semi standard non polar33892256
Hydantoin-5-propionic acid,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)C1CCC(=O)O1912.7Semi standard non polar33892256
Hydantoin-5-propionic acid,1TMS,isomer #3C[Si](C)(C)N1C(=O)NC(CCC(=O)O)C1=O1907.1Semi standard non polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1C(=O)NC(=O)N1[Si](C)(C)C1980.7Semi standard non polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1C(=O)NC(=O)N1[Si](C)(C)C1948.4Standard non polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC1C(=O)NC(=O)N1[Si](C)(C)C3405.5Standard polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCC1NC(=O)N([Si](C)(C)C)C1=O1988.8Semi standard non polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCC1NC(=O)N([Si](C)(C)C)C1=O1930.9Standard non polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCC1NC(=O)N([Si](C)(C)C)C1=O3347.6Standard polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #3C[Si](C)(C)N1C(=O)C(CCC(=O)O)N([Si](C)(C)C)C1=O1859.2Semi standard non polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #3C[Si](C)(C)N1C(=O)C(CCC(=O)O)N([Si](C)(C)C)C1=O1842.1Standard non polar33892256
Hydantoin-5-propionic acid,2TMS,isomer #3C[Si](C)(C)N1C(=O)C(CCC(=O)O)N([Si](C)(C)C)C1=O2593.4Standard polar33892256
Hydantoin-5-propionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCC1C(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C1862.5Semi standard non polar33892256
Hydantoin-5-propionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCC1C(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C1923.0Standard non polar33892256
Hydantoin-5-propionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCC1C(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C2342.7Standard polar33892256
Hydantoin-5-propionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1NC(=O)NC1=O2161.3Semi standard non polar33892256
Hydantoin-5-propionic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1CCC(=O)O2176.1Semi standard non polar33892256
Hydantoin-5-propionic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)NC(CCC(=O)O)C1=O2154.9Semi standard non polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1C(=O)NC(=O)N1[Si](C)(C)C(C)(C)C2477.0Semi standard non polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1C(=O)NC(=O)N1[Si](C)(C)C(C)(C)C2392.2Standard non polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1C(=O)NC(=O)N1[Si](C)(C)C(C)(C)C3337.9Standard polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC1NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2451.1Semi standard non polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC1NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2374.2Standard non polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC1NC(=O)N([Si](C)(C)C(C)(C)C)C1=O3214.3Standard polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)C(CCC(=O)O)N([Si](C)(C)C(C)(C)C)C1=O2321.2Semi standard non polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)C(CCC(=O)O)N([Si](C)(C)C(C)(C)C)C1=O2282.9Standard non polar33892256
Hydantoin-5-propionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)C(CCC(=O)O)N([Si](C)(C)C(C)(C)C)C1=O2616.8Standard polar33892256
Hydantoin-5-propionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2545.1Semi standard non polar33892256
Hydantoin-5-propionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2569.4Standard non polar33892256
Hydantoin-5-propionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C2573.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Hydantoin-5-propionic acid GC-MS (3 TMS)splash10-0a4i-3961000000-07de24d94e2304e2b5972014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydantoin-5-propionic acid GC-MS (4 TMS)splash10-0059-3519000000-2edee3d23ebfb1aed3062014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydantoin-5-propionic acid GC-MS (Non-derivatized)splash10-0a4i-3961000000-07de24d94e2304e2b5972017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydantoin-5-propionic acid GC-MS (Non-derivatized)splash10-0059-3519000000-2edee3d23ebfb1aed3062017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydantoin-5-propionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-9600000000-72cc8eb79a0737df29a02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydantoin-5-propionic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00ba-9720000000-c1c0fbcd1ed84d9507ac2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydantoin-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 - Hydantoin-5-propionic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-19934f3de22343e3db0e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 20V, Positive-QTOFsplash10-0pc0-5900000000-c3114ac773b2d9b752702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-46959f6a9b40876211872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 10V, Negative-QTOFsplash10-00di-0900000000-4fb2343d2f66db0c68902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 20V, Negative-QTOFsplash10-0ffx-4900000000-6c01203d4c8c99cf8f6c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 40V, Negative-QTOFsplash10-0006-9000000000-d153c6a3d156a466ad592017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 10V, Negative-QTOFsplash10-00di-0900000000-5ee56d718be837eede1e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 20V, Negative-QTOFsplash10-0006-9300000000-4798e4cff31bc0a178e62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 40V, Negative-QTOFsplash10-0006-9000000000-f929846fd3d130f328a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 10V, Positive-QTOFsplash10-00di-0900000000-4e0de47e878bed79a35b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 20V, Positive-QTOFsplash10-004i-2900000000-4150d50600586f3cb1482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydantoin-5-propionic acid 40V, Positive-QTOFsplash10-00kf-9000000000-18812b534520e16613162021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022493
KNApSAcK IDNot Available
Chemspider ID761
KEGG Compound IDC05565
BioCyc IDHYDANTOIN-5-PROPIONATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6084
PubChem Compound782
PDB IDNot Available
ChEBI ID28297
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHassall, H.; Greenberg, D. M. Preparation of carbamylglutamic acid and hydantoin-5-propionic acid. Methods Enzymol. (1971), 17(Pt. B), 95-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Duran M, Bruinvis L, Wadman SK: Quantitative gas chromatographic determination of urinary hydantoin-5-propionic acid in patients with disorders of folate/vitamin B12 metabolism. J Chromatogr. 1986 Sep 5;381(2):401-5. [PubMed:3760095 ]
  2. Duran M, Dorland L, Meuleman EE, Renardel de Lavalette PA, Poll-The BT, Berger R: Formiminoglutamic/hydantoinpropionic aciduria in two siblings. J Inherit Metab Dis. 1993;16(1):155-6. [PubMed:8487495 ]