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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
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
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

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.
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).