Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-08-16 18:04:17 UTC |
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NP-MRD ID | NP0000333 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Ureidosuccinic acid |
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Description | Ureidosuccinic acid, also known as L-ureidosuccinate or carbamyl-L-aspartate, belongs to the class of organic compounds known as aspartic acids and derivatives. Aspartic acids 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 also classified as a carbamate derivative. It is a solid that is soluble in water. Ureidosuccinic acid exists in all living species, ranging from bacteria to plants to humans. Ureidosuccinic acid can be biosynthesized from carbamoyl phosphate and L-aspartic acid through the action of the enzyme known as aspartate carbamoyltransferase (ACTase) and serves as an intermediate in pyrimidine biosynthesis. In humans, a drop in the level of urinary ureidosuccinic acid is associated with bladder cancer (PMID: 25562196 ). It is also involved in the metabolic disorder called Canavan disease. |
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Structure | NC(=O)N[C@@H](CC(O)=O)C(O)=O 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 |
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Synonyms | Value | Source |
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Carbamyl-L-aspartic acid | ChEBI | L-Ureidosuccinic acid | ChEBI | N-(Aminocarbonyl)-L-aspartic acid | ChEBI | N-Carbamoyl-L-aspartate | ChEBI | N-Carbamoyl-S-aspartic acid | ChEBI | Carbamyl-L-aspartate | Generator | L-Ureidosuccinate | Generator | N-(Aminocarbonyl)-L-aspartate | Generator | N-Carbamoyl-L-aspartic acid | Generator | N-Carbamoyl-S-aspartate | Generator | Ureidosuccinate | Generator | 2-Ureidobutanedioate | HMDB | 2-Ureidobutanedioic acid | HMDB | Carbamoylaspartic acid | HMDB | Carbamylaspartic acid | HMDB | L-N-Carbamoylaspartic acid | HMDB | N-Carbamoylaspartate | HMDB | N-Carbamoylaspartic acid | HMDB | NCD | HMDB | Carbamyl-DL-aspartate | HMDB | Ureidosuccinic acid, (D)-isomer | HMDB | Ureidosuccinic acid, maganeese (+2), (1:1) salt | HMDB | Ureidosuccinic acid, zinc (1:1) salt, (L)-isomer | HMDB | N-Carbamoyl-D-aspartic acid | HMDB | Ureidosuccinic acid, (L)-isomer | HMDB | Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomer | HMDB |
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Chemical Formula | C5H8N2O5 |
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Average Mass | 176.1274 Da |
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Monoisotopic Mass | 176.04332 Da |
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IUPAC Name | (2S)-2-(carbamoylamino)butanedioic acid |
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Traditional Name | carbamylaspartic acid |
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CAS Registry Number | 13184-27-5 |
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SMILES | NC(=O)N[C@@H](CC(O)=O)C(O)=O |
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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 |
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InChI Key | HLKXYZVTANABHZ-REOHCLBHSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, simulated) | Varshavi.d26 | | | 2021-08-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Varshavi.d26 | | | 2021-08-23 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, simulated) | Varshavi.d26 | | | 2021-08-07 | View Spectrum |
| Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Aspartic acid and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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 |
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Predicted Properties | |
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General References | - 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
- 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 ]
- Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]
- Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]
- Shen C, Sun Z, Chen D, Su X, Jiang J, Li G, Lin B, Yan J: Developing urinary metabolomic signatures as early bladder cancer diagnostic markers. OMICS. 2015 Jan;19(1):1-11. doi: 10.1089/omi.2014.0116. [PubMed:25562196 ]
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