Record Information
Version2.0
Creation Date2012-05-31 13:03:19 -0600
Update Date2015-06-03 15:53:39 -0600
Secondary Accession Numbers
  • ECMDB01005
Identification
Name:(S)-Ureidoglycolic acid
Description:(S)-Ureidoglycolic acid is a substrate of enzyme ureidoglycolate dehydrogenase [EC 1.1.1.154] in purine metabolism pathway (KEGG). Enteric bacteria such as E. coli are able to utilize allantoin as a sole source of nitrogen under anaerobic conditions, but cannot utilize it as a sole source of carbon The first step in allantoin degradation is the opening of the aromatic ring, yielding allantoate, performed by allantoinase. In the next step allantoate is hydrolyzed to S-ureidoglycine by allantoate amidohydrolase. Ureidoglycine spontaneously converts to Ureidoglycolate. Ureidoglycolate dehydrogenase then oxidizes ureidoglycolate to oxalurate. It is believed oxalurate is converted into oxamate and carbamoyl-phosphate, which can be further metabolized to CO2, ammonia and ATP.
Structure
Thumb
Synonyms:
  • (-)-Ureidoglycolate
  • (-)-Ureidoglycolic acid
  • (S)-Ureidoglycolate
  • (S)-Ureidoglycolic acid
  • (S)-[(aminocarbonyl)amino]hydroxy-acetate
  • (S)-[(aminocarbonyl)amino]hydroxy-acetic acid
  • S-ureidoglycolate
  • S-(-)-Ureidoglycolate
  • S-(-)-Ureidoglycolic acid
  • S-Ureidoglycolate
  • S-Ureidoglycolic acid
  • Ureidoglycolate
  • Ureidoglycolic acid
Chemical Formula:C3H6N2O4
Weight:Average: 134.0907
Monoisotopic: 134.03275669
InChI Key:NWZYYCVIOKVTII-SFOWXEAESA-N
InChI:InChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)/t1-/m0/s1
CAS number:7424-03-5
IUPAC Name:(2S)-2-(carbamoylamino)-2-hydroxyacetic acid
Traditional IUPAC Name:ureidoglycolate
SMILES:NC(=O)N[C@@H](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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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 Locations:Cytoplasm
Reactions:
SMPDB Pathways:
allantoin degradation (anaerobic)PW002050 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolate and glyoxylate degradationPW000827 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • allantoin degradation IV (anaerobic) PWY0-41
  • allantoin degradation to glyoxylate III PWY-5705
  • allantoin degradation to ureidoglycolate II (ammonia producing) PWY-5698
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r6-9100000000-a7e6b112e52795850588View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02mi-8920000000-76af510166ac80995acdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9700000000-3a4e2e6ced0b05835ca9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-f71cc7c577d24a593825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9000000000-8e08566417cf9479b434View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9100000000-b163bec3ba10c56f6646View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-9777b17cbceaafa658b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e546d2761ff46042436bView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15412
HMDB IDHMDB01005
Pubchem Compound ID439269
Kegg IDC00603
ChemSpider ID388403
Wikipedia IDNot Available
BioCyc IDCPD-1091
EcoCyc IDCPD-1091

Enzymes

General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Involved in the anaerobic utilization of allantoin. Converts allantoate to (S)-ureidoglycolate and ammonia
Gene Name:
allC
Uniprot ID:
P77425
Molecular weight:
45694
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the anaerobic utilization of allantoin
Gene Name:
allD
Uniprot ID:
P77555
Molecular weight:
37967
Reactions
(S)-ureidoglycolate + NAD(P)(+) = oxalureate + NAD(P)H.
General function:
Involved in ureidoglycolate hydrolase activity
Specific function:
Involved in the anaerobic utilization of allantoin. Reinforces the induction of genes involved in the degradation of allantoin and glyoxylate by producing glyoxylate
Gene Name:
allA
Uniprot ID:
P77731
Molecular weight:
18169
Reactions
(S)-ureidoglycolate + H(2)O = glyoxylate + 2 NH(3) + CO(2).
General function:
Not Available
Specific function:
Not Available
Gene Name:
ylbA
Uniprot ID:
P75713
Molecular weight:
Not Available