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Human Metabolome Database Version 3.5

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Showing metabocard for Ureidosuccinic acid (HMDB00828)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:24 -0700
HMDB ID HMDB00828
Secondary Accession Numbers None
Metabolite Identification
Common Name Ureidosuccinic acid
Description Ureidosuccinic acid is an intermediary product in pyrimidine biosynthesis.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Ureidobutanedioate
  2. 2-Ureidobutanedioic acid
  3. Carbamoylaspartic acid
  4. Carbamyl-L-aspartic acid
  5. Carbamylaspartic acid
  6. L-N-Carbamoylaspartic acid
  7. L-Ureidosuccinate
  8. L-Ureidosuccinic acid
  9. N-(Aminocarbonyl)-L-aspartic acid
  10. N-Carbamoyl-L-aspartate
  11. N-Carbamoyl-L-aspartic acid
  12. N-Carbamoyl-S-aspartic acid
  13. N-Carbamoylaspartate
  14. N-Carbamoylaspartic acid
  15. NCD
  16. Ureidosuccinate
Chemical Formula C5H8N2O5
Average Molecular Weight 176.1274
Monoisotopic Molecular Weight 176.043321376
IUPAC Name (2S)-2-(carbamoylamino)butanedioic acid
Traditional IUPAC Name N-carbamoyl-L-aspartate
CAS Registry Number 13184-27-5
SMILES NC(=O)N[C@@H](CC(O)=O)C(O)=O
InChI Identifier 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
InChI Key HLKXYZVTANABHZ-REOHCLBHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • N-carbamoyl-amino acid(ChEBI)
  • Organic Compounds
  • aspartic acid derivative(ChEBI)
Substituents
  • 1,3 Aminoalcohol
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Succinic Acid
  • Urea
Direct Parent N-carbamoyl-alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 174 - 175 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.7 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 21.3 g/L ALOGPS
LogP -1.12 ALOGPS
LogP -1.7 ChemAxon
LogS -0.92 ALOGPS
pKa (strongest acidic) 3.33 ChemAxon
pKa (strongest basic) -2.6 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 129.72 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 34.65 ChemAxon
Polarizability 14.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Prostate Tissue
Tissue Location
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Pyrimidine Metabolism SMP00046 map00240 Link_out
Aspartate Metabolism SMP00067 map00250 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Prostate Tissue Detected and Quantified
Article_icon
0.5 (0.0-1.0) umol/g tissue Adult (>18 years old) Both Prostate Cancer Estimated concentration
Associated Disorders and Diseases
Disease References
Prostate cancer
  • 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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022269
    KNApSAcK ID Not Available
    Chemspider ID 84022 Link_out
    KEGG Compound ID C00438 Link_out
    BioCyc ID CARBAMYUL-L-ASPARTATE Link_out
    BiGG ID 34984 Link_out
    Wikipedia Link NCD Link_out
    NuGOwiki Link HMDB00828 Link_out
    Metagene Link HMDB00828 Link_out
    METLIN ID 5791 Link_out
    PubChem Compound 93072 Link_out
    PDB ID NCD Link_out
    ChEBI ID 15859 Link_out
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. 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 Link_out
    2. 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 Link_out
    3. 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 Link_out
    Enzymes
    Name: Aspartyl-tRNA synthetase, cytoplasmic
    Reactions:
    • ATP + L-aspartate + tRNAAsp = AMP + diphosphate + L-aspartyl-tRNAAsp [RN:R05577]
    Gene Name: DARS
    Uniprot ID: P14868 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glutamate decarboxylase 1
    Reactions:
    • L-glutamate = 4-aminobutanoate + CO2 [RN:R00261]
    Gene Name: GAD1
    Uniprot ID: Q99259 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: CAD protein
    Reactions:
    • (1) 2 ATP + L-glutamine + HCO3- + H2O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate [RN:R00575]
    • (2) L-glutamine + H2O = L-glutamate + NH3 [RN:R00256]
    • (3) 2 ATP + HCO3- = 2 ADP + phosphate + carbamoyl phosphate [RN:R07641]
    Gene Name: CAD
    Uniprot ID: P27708 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA