(S)-Ureidoglycolic acid (YMDB00377)

Identification
YMDB IDYMDB00377
Name(S)-Ureidoglycolic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-Ureidoglycolic acid is an hydrolysis product of allantoate in the allantoin degradation to glyoxylate pathway. Allantoin is a common product of purine degradation. Allantoin is rich in nitrogen and many organisms are able to degrade it and recycle it. Yeast can use allantoin as sole nitrogen source by degrading it to urea, CO2 and glyoxylate. Urea is further degraded to ammonia. [Biocyc PWY-5694]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (-)-Ureidoglycolate
  • (-)-Ureidoglycolic acid
  • (S)-[(aminocarbonyl)amino]hydroxy-acetic acid
  • (S)-Ureidoglycolate
  • (S)-Ureidoglycolic acid
  • S-(-)-Ureidoglycolic acid
  • ureidoglycolate
CAS number7424-03-5
WeightAverage: 134.0907
Monoisotopic: 134.03275669
InChI KeyNWZYYCVIOKVTII-SFOWXEAESA-N
InChIInChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)/t1-/m0/s1
IUPAC Name(2S)-2-(carbamoylamino)-2-hydroxyacetic acid
Traditional IUPAC Nameureidoglycolate
Chemical FormulaC3H6N2O4
SMILES[H]OC(=O)[C@]([H])(O[H])N([H])C(=O)N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-carbamoyl-alpha amino acids
Alternative Parents
Substituents
  • N-carbamoyl-alpha-amino acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Carbonic acid derivative
  • Urea
  • Alkanolamine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility67.9 g/LALOGPS
logP-2.1ALOGPS
logP-2ChemAxon
logS-0.3ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area112.65 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.32 m³·mol⁻¹ChemAxon
Polarizability10.8 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r6-9100000000-a7e6b112e52795850588JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02mi-8920000000-76af510166ac80995acdJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9700000000-3a4e2e6ced0b05835ca9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-f71cc7c577d24a593825JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9000000000-8e08566417cf9479b434JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9100000000-b163bec3ba10c56f6646JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-9777b17cbceaafa658b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e546d2761ff46042436bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9100000000-f83fb023b339c1a74e1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-10d946d055df2a11aaceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9500000000-098f8ca862d2f98d80adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h2f-9200000000-2b972ed857e447394a61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-940f7cfcfa787f6857aeJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15412
HMDB IDHMDB01005
Pubchem Compound ID439269
Kegg IDC00603
ChemSpider ID388403
FOODB IDFDB022364
Wikipedia IDNot Available
BioCyc IDCPD-1091

Enzymes

Protein Details
1. Allantoicase
General function:
Involved in allantoicase activity
Specific function:
Utilization of purines as secondary nitrogen sources, when primary sources are limiting
Gene Name:
DAL2
Uniprot ID:
P25335
Molecular weight:
38713.5
Reactions
Allantoate + H(2)O → (S)-ureidoglycolate + urea.
Protein Details
2. Ureidoglycolate hydrolase
General function:
Involved in ureidoglycolate hydrolase activity
Specific function:
Utilization of purines as secondary nitrogen sources, when primary sources are limiting
Gene Name:
DAL3
Uniprot ID:
P32459
Molecular weight:
21726.59961
Reactions
(S)-ureidoglycolate + H(2)O → glyoxylate + 2 NH(3) + CO(2).