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Identification
YMDB IDYMDB00027
NameUreidosuccinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUreidosuccinic acid, also known as L-ureidosuccinate or carbamyl-L-aspartate, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Ureidosuccinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Ureidosuccinic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 2-Ureidobutanedioate
  • 2-Ureidobutanedioic acid
  • Aspartic acid, N-carbamoyl-
  • Aspartic acid, N-carbamoyl-, L-
  • Carbamoylaspartic acid
  • Carbamyl-L-aspartate
  • Carbamyl-l-aspartic acid
  • Carbamylaspartic acid
  • L-Aspartic acid, N-(aminocarbonyl)-
  • L-n-carbamoylaspartic acid
  • L-ureidosuccinate
  • L-ureidosuccinic acid
  • N-(Aminocarbonyl)-L-aspartate
  • N-(aminocarbonyl)-l-aspartic acid
  • N-(aminocarbonyl)aspartic acid
  • N-carbamoyl-l-aspartate
  • N-carbamoyl-l-aspartic acid
  • N-Carbamoyl-S-aspartate
  • N-carbamoyl-s-aspartic acid
  • N-carbamoylaspartate
  • N-carbamoylaspartic acid
  • NCD
  • Succinic acid, ureido-
  • Ureidosuccinate
  • Ureidosuccinic acid
  • Carbamyl-DL-aspartate
  • Ureidosuccinic acid, (D)-isomer
  • Ureidosuccinic acid, maganeese (+2), (1:1) salt
  • Ureidosuccinic acid, zinc (1:1) salt, (L)-isomer
  • N-Carbamoyl-D-aspartic acid
  • Ureidosuccinic acid, (L)-isomer
  • Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomer
CAS number13184-27-5
WeightAverage: 176.1274
Monoisotopic: 176.043321376
InChI KeyHLKXYZVTANABHZ-REOHCLBHSA-N
InChIInChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)/t2-/m0/s1
IUPAC Name(2S)-2-(carbamoylamino)butanedioic acid
Traditional IUPAC Namecarbamylaspartic acid
Chemical FormulaC5H8N2O5
SMILES[H]OC(=O)C([H])([H])[C@]([H])(N([H])C(=O)N([H])[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Isourea
  • Carboximidamide
  • Carboxylic acid
  • Carboximidic acid derivative
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point174 - 175 °C
Experimental Properties
PropertyValueReference
Water Solubility3.7 mg/mL [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility21.3 g/LALOGPS
logP-1.1ALOGPS
logP-1.7ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.65 m³·mol⁻¹ChemAxon
Polarizability14.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Organoleptic PropertiesNot Available
SMPDB Pathways
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Pyrimidine metabolismec00240 Map00240
SMPDB ReactionsNot Available
KEGG Reactions
L-Aspartic acid + CarbamoylphosphateUreidosuccinic acid + phosphate + hydron
water + L-Dihydroorotic acidUreidosuccinic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f89-3940000000-f6b458a8d8c1bb66550aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-03di-1910000000-8a8dd39c35aa7c99f81aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0920000000-cdbae9a5c80fb0023f8eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f89-3940000000-f6b458a8d8c1bb66550aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-1910000000-8a8dd39c35aa7c99f81aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0016-9600000000-c3f9041273a7b07c96adJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9661000000-59d277eae56bc52aa7faJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-2900000000-8579bc85efea27463b1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-bfd715a5dec069d32aeaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-17769f0943f627a57c64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0059-0900000000-d1e136c596eda61fdad6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-d9c4b6edb79ec7db500cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9500000000-8a0f02bbd32fdd0af067JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-c1e7be64cc9ef25c1291JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-d90115a5ff29ff776135JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-0900000000-d1e136c596eda61fdad6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-d9c4b6edb79ec7db500cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9500000000-ec02387ba0107a9f05cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9100000000-c1e7be64cc9ef25c1291JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d90115a5ff29ff776135JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057i-1900000000-e642a1d611b0cd263a5bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0310-8900000000-0ed6a7e85a30fafb07b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9100000000-48fee59912455e39938aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-6900000000-9bae4efc52500be1a047JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001c-9400000000-0fc35cb79f71cc7fbdf1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-27e270ecc918b43d4a41JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Drillien, R., Lacroute, F. (1972). "Ureidosuccinic acid uptake in yeast and some aspects of its regulation." J Bacteriol 109:203-208.4550662
  • Guyonvarch, A., Nguyen-Juilleret, M., Hubert, J. C., Lacroute, F. (1988). "Structure of the Saccharomyces cerevisiae URA4 gene encoding dihydroorotase." Mol Gen Genet 212:134-141.2897615
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15859
HMDB IDHMDB00828
Pubchem Compound ID93072
Kegg IDC00438
ChemSpider ID84022
FOODB IDFDB022269
Wikipedia IDCarbamoyl_aspartic_acid
BioCyc IDCARBAMYUL-L-ASPARTATE

Enzymes

General function:
Involved in carboxyl- or carbamoyltransferase activity
Specific function:
This protein is a "fusion" protein encoding three enzymatic activities of the pyrimidine pathway (GATase, CPSase, and ATCase)
Gene Name:
URA2
Uniprot ID:
P07259
Molecular weight:
245124.0
Reactions
2 ATP + L-glutamine + HCO(3)(-) + H(2)O → 2 ADP + phosphate + L-glutamate + carbamoyl phosphate.
Carbamoyl phosphate + L-aspartate → phosphate + N-carbamoyl-L-aspartate.
General function:
Involved in dihydroorotase activity
Specific function:
(S)-dihydroorotate + H(2)O = N-carbamoyl-L- aspartate
Gene Name:
URA4
Uniprot ID:
P20051
Molecular weight:
40313.0
Reactions
(S)-dihydroorotate + H(2)O → N-carbamoyl-L-aspartate.