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Record Information

Version

2.0

Creation Date

2012-05-31 13:03:19 -0600

Update Date

2015-06-03 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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-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 Framework

Aliphatic acyclic compounds

External Descriptors

ureidoglycolic acid (CHEBI:15412 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	67.9 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	2.94	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.32 m³·mol⁻¹	ChemAxon
Polarizability	10.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

allantoin degradation (anaerobic)	PW002050
glycolate and glyoxylate degradation	PW000827

KEGG Pathways:

Microbial metabolism in diverse environments ec01120
Purine metabolism ec00230

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 Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01r6-9100000000-a7e6b112e52795850588	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-02mi-8920000000-76af510166ac80995acd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9700000000-3a4e2e6ced0b05835ca9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9000000000-f71cc7c577d24a593825	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9000000000-8e08566417cf9479b434	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9100000000-b163bec3ba10c56f6646	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052f-9000000000-9777b17cbceaafa658b0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e546d2761ff46042436b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9100000000-f83fb023b339c1a74e1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-10d946d055df2a11aace	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9500000000-098f8ca862d2f98d80ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h2f-9200000000-2b972ed857e447394a61	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-940f7cfcfa787f6857ae	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

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

Links

External Links:

Resource	Link
CHEBI ID	15412
HMDB ID	HMDB01005
Pubchem Compound ID	439269
Kegg ID	C00603
ChemSpider ID	388403
Wikipedia ID	Not Available
BioCyc ID	CPD-1091
EcoCyc ID	CPD-1091

Enzymes

Protein Details

1. Allantoate amidohydrolase

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

Protein Details

2. Ureidoglycolate dehydrogenase

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.

Protein Details

3. 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
Uniprot ID:: P77731
Molecular weight:: 18169

Reactions

(S)-ureidoglycolate + H(2)O = glyoxylate + 2 NH(3) + CO(2).

Protein Details

4. conserved protein

General function:: Not Available
Specific function:: Not Available
Gene Name:: ylbA
Uniprot ID:: P75713
Molecular weight:: Not Available

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(S)-Ureidoglycolic acid (M2MDB000223)

Structure for #<Compound:0xa946ba14>

Enzymes

Reactions

Reactions