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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:49 UTC
HMDB IDHMDB0001212
Secondary Accession Numbers
  • HMDB01212
Metabolite Identification
Common NameHydantoin-5-propionic acid
DescriptionHydantoin-5-propionic acid is a metabolite of histidine, urinary hydantoin-5-propionic acid occur in patients with disorders of folate/ vitamin B12 metabolism (PMID: 3760095 ). Folic acid non-dependent excessive formiminoglutamic aciduria (Figlu-uria) is an extremely rare disorder; treatment with oral folate supplements (15 mg/day) for 3 weeks failed to reduce urinary hydantoin-5-propionic acid (PMID: 8487495 ).
Structure
Thumb
Synonyms
ValueSource
Hydantoin-propionateKegg
Hydantoin-propionic acidGenerator
Hydantoin-5-propionateGenerator
1-(2,4-(3H,5H)Imidazoledione)propionic acidMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • 5-monosubstituted hydantoin
  • Ureide
  • Dicarboximide
  • Urea
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-3961000000-07de24d94e2304e2b597View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0059-3519000000-2edee3d23ebfb1aed306View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-3961000000-07de24d94e2304e2b597View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-3519000000-2edee3d23ebfb1aed306View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-9600000000-72cc8eb79a0737df29a0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ba-9720000000-c1c0fbcd1ed84d9507acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-19934f3de22343e3db0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-5900000000-c3114ac773b2d9b75270View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-46959f6a9b4087621187View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4fb2343d2f66db0c6890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ffx-4900000000-6c01203d4c8c99cf8f6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d153c6a3d156a466ad59View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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 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 ]