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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:46:28 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?1582752184
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
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available139.42731661259
DarkChem[M-H]-PredictedNot Available131.20131661259
AllCCS[M+H]+PredictedNot Available136.88832859911
AllCCS[M-H]-PredictedNot Available132.5932859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Hydantoin-5-propionic acid,1TMS,#11915.751https://arxiv.org/abs/1905.12712
Hydantoin-5-propionic acid,1TMS,#21912.7494https://arxiv.org/abs/1905.12712
Hydantoin-5-propionic acid,1TMS,#31907.0662https://arxiv.org/abs/1905.12712
Hydantoin-5-propionic acid,1TBDMS,#12161.293https://arxiv.org/abs/1905.12712
Hydantoin-5-propionic acid,1TBDMS,#22176.0967https://arxiv.org/abs/1905.12712
Hydantoin-5-propionic acid,1TBDMS,#32154.8691https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-3961000000-07de24d94e2304e2b5972014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0059-3519000000-2edee3d23ebfb1aed3062014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-3961000000-07de24d94e2304e2b5972017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-3519000000-2edee3d23ebfb1aed3062017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-9600000000-72cc8eb79a0737df29a02017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ba-9720000000-c1c0fbcd1ed84d9507ac2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-19934f3de22343e3db0e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-5900000000-c3114ac773b2d9b752702017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-46959f6a9b40876211872017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4fb2343d2f66db0c68902017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ffx-4900000000-6c01203d4c8c99cf8f6c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d153c6a3d156a466ad592017-09-01View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
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
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 ]