| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 2-Ureidobutanedioate
- 2-Ureidobutanedioic acid
- Carbamoylaspartic acid
- Carbamyl-L-aspartic acid
- Carbamylaspartic acid
- L-N-Carbamoylaspartic acid
- L-Ureidosuccinate
- L-Ureidosuccinic acid
- N-(Aminocarbonyl)-L-aspartic acid
- N-Carbamoyl-L-aspartate
- N-Carbamoyl-L-aspartic acid
- 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 |
| 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 |
|
| Biofunction |
- Protein synthesis, amino acid biosynthesis
|
| Application |
Not Available |
| Cellular locations |
|
| 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 |
|
| Spectra |
|
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| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
|
| Tissue Location |
|
| Pathways |
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| Normal Concentrations |
|
Not Available |
| Abnormal Concentrations |
|
| Prostate Tissue |
Detected and Quantified |
|
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
|
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| Associated OMIM IDs |
|
| External Links |
| 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  |
| KEGG Compound ID |
C00438  |
| BioCyc ID |
CARBAMYUL-L-ASPARTATE  |
| BiGG ID |
34984  |
| Wikipedia Link |
NCD  |
| NuGOwiki Link |
HMDB00828  |
| Metagene Link |
HMDB00828  |
| METLIN ID |
5791  |
| PubChem Compound |
93072  |
| PDB ID |
NCD  |
| ChEBI ID |
15859  |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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
- 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
- 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
|