(S)-Ureidoglycolic acid (PAMDB000223)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000223
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 Pseudomonas aeruginosa 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 134.0907
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent N-carbamoyl-alpha amino acids
Alternative Parents
Substituents
  • N-carbamoyl-alpha-amino acid
  • Ureide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Urea
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility67.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.32 m3·mol-1ChemAxon
Polarizability10.8 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2 Hydrogen ion + Water + (S)-Ureidoglycolic acid > Carbon dioxide + Glyoxylic acid +2 Ammonium
Allantoic acid + 2 Hydrogen ion + 2 Water > Carbon dioxide +2 Ammonium + (S)-Ureidoglycolic acid
NAD + (S)-Ureidoglycolic acid <> Hydrogen ion + NADH + Oxalureate
(S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide
(S)-Ureidoglycolic acid + NADP <> Oxalureate + NADPH + Hydrogen ion
Ureidoglycine + Water <> (S)-Ureidoglycolic acid + Ammonia
NAD(P)<sup>+</sup> + (S)-Ureidoglycolic acid > NAD(P)H + Oxalureate + Hydrogen ion
(S)-Ureidoglycolic acid > Urea + Glyoxylic acid
<i>S</i>-ureidoglycine + Water > Hydrogen ion + Ammonia + (S)-Ureidoglycolic acid
(S)-Ureidoglycolic acid + NAD(P)(+) > Oxalureate + NAD(P)H
(S)-Ureidoglycolic acid + NAD + NADP <> Oxalureate + NADH + NADPH + Hydrogen ion
S-ureidoglycine + Water > Ammonium + (S)-Ureidoglycolic acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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

Protein Details
• Ureidoglycolate hydrolase
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
Locus Tag:
PA1514
Molecular weight:
19 kDa
Reactions
(S)-ureidoglycolate + H(2)O = glyoxylate + 2 NH(3) + CO(2).