Ureidosuccinic acid (PAMDB000189)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000189
Identification
Name: Ureidosuccinic acid
Description:Ureidosuccinic acid is an intermediary product in pyrimidine metabolism. It is generated by the action of dihydroorotase which catalyzes the following reaction: 4,5-Dihydroorotic acid + Water <=> Ureidosuccinic acid + H+
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Ureidobutanedioate
  • 2-Ureidobutanedioic acid
  • Carbamoyl-Asp
  • Carbamoyl-aspartate
  • Carbamoyl-aspartic acid
  • Carbamoylaspartate
  • Carbamoylaspartic acid
  • Carbamyl-aspartate
  • Carbamyl-aspartic acid
  • Carbamyl-L-aspartate
  • Carbamyl-L-aspartic acid
  • Carbamylaspartate
  • Carbamylaspartic acid
  • Carbamyul-aspartate
  • Carbamyul-aspartic acid
  • Carbamyul-L-aspartate
  • Carbamyul-L-aspartic acid
  • L-N-Carbamoylaspartate
  • L-N-Carbamoylaspartic acid
  • L-Ureidosuccinate
  • L-Ureidosuccinic acid
  • N-(Aminocarbonyl)-L-aspartate
  • N-(Aminocarbonyl)-L-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
  • Ureidosuccinate
Chemical Formula: C5H8N2O5
Average Molecular Weight: 176.1274
Monoisotopic Molecular Weight: 176.043321376
InChI Key: HLKXYZVTANABHZ-REOHCLBHSA-N
InChI:InChI=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
CAS number: 13184-27-5
IUPAC Name:(2S)-2-(carbamoylamino)butanedioic acid
Traditional IUPAC Name: carbamylaspartic acid
SMILES:NC(=O)N[C@@H](CC(O)=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
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Urea
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 174 - 175 °C
Experimental Properties:
PropertyValueSource
Water Solubility:3.7 mg/mL [BEILSTEIN]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility21.3 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.65 m3·mol-1ChemAxon
Polarizability14.72 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
L-Aspartic acid + Carbamoylphosphate <> Ureidosuccinic acid + Hydrogen ion + Phosphate
4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid + Hydrogen ion
Carbamoylphosphate + L-Aspartic acid <> Phosphate + Ureidosuccinic acid
4,5-Dihydroorotic acid + Water <> Ureidosuccinic acid
Carbamoylphosphate + L-Aspartic acid > Inorganic phosphate + Ureidosuccinic acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f89-3940000000-f6b458a8d8c1bb66550aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-03di-1910000000-8a8dd39c35aa7c99f81aView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-2900000000-8579bc85efea27463b1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-bfd715a5dec069d32aeaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-17769f0943f627a57c64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0059-0900000000-d1e136c596eda61fdad6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-d9c4b6edb79ec7db500cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9500000000-8a0f02bbd32fdd0af067View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-9100000000-c1e7be64cc9ef25c1291View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-d90115a5ff29ff776135View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • 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
  • Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van Kuilenburg AB, van Lenthe H, Loffler M, van Gennip AH: Analysis of pyrimidine synthesis "de novo" intermediates in urine and dried urine filter- paper strips with HPLC-electrospray tandem mass spectrometry. Clin Chem. 2004 Nov;50(11):2117-24. Epub 2004 Sep 16. Pubmed: 15375016
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15859
HMDB IDHMDB00828
Pubchem Compound ID93072
Kegg IDC00438
ChemSpider ID84022
WikipediaCarbamoyl_aspartic_acid
BioCyc IDCARBAMYUL-L-ASPARTATE
EcoCyc IDCARBAMYUL-L-ASPARTATE
Ligand ExpoNCD

Enzymes

Protein Details
• Dihydroorotase
General function:
Involved in hydrolase activity
Specific function:
(S)-dihydroorotate + H(2)O = N-carbamoyl-L- aspartate
Gene Name:
pyrC
Locus Tag:
PA3527
Molecular weight:
38.4 kDa
Reactions
(S)-dihydroorotate + H(2)O = N-carbamoyl-L-aspartate.
Protein Details
• Aspartate carbamoyltransferase catalytic chain
General function:
Involved in carboxyl- or carbamoyltransferase activity
Specific function:
Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate
Gene Name:
pyrB
Locus Tag:
PA0402
Molecular weight:
36.6 kDa
Reactions
Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate.