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Identification
YMDB IDYMDB01042
NameUreidoglycolic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer'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
Synonyms
  • Ureidoglycolate
  • (+)-Ureidoglycolate
  • (+)-Ureidoglycolic acid
CAS numberNot Available
WeightAverage: 134.0907
Monoisotopic: 134.03275669
InChI KeyNWZYYCVIOKVTII-UHFFFAOYSA-N
InChIInChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)
IUPAC Name2-hydroxy-2-[(C-hydroxycarbonimidoyl)amino]acetic acid
Traditional IUPAC Namehydroxy(C-hydroxycarbonimidoylamino)acetic acid
Chemical FormulaC3H6N2O4
SMILESNC(=O)NC(O)C(O)=O
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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.48 g/LALOGPS
logP-1.8ALOGPS
logP-2.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area113.64 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.26 m³·mol⁻¹ChemAxon
Polarizability10.81 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
Allantoic acid + waterUrea + Ureidoglycolic acid
water + hydron + Ureidoglycolic acidGlyoxylic acid + Carbon dioxide + Ammonium
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Lawther, R. P., Riemer, E., Chojnacki, B., Cooper, T. G. (1974). "Clustering of the genes for allantoin degradation in Saccharomyces cerevisiae." J Bacteriol 119:461-468.4604238
  • Yoo, H. S., Cooper, T. G. (1991). "The ureidoglycollate hydrolase (DAL3) gene in Saccharomyces cerevisiae." Yeast 7:693-698.1776360
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID49050
HMDB IDNot Available
Pubchem Compound ID16219415
Kegg IDC05241
ChemSpider ID329
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD-1091