Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:24:55 UTC |
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Update date | 2015-10-09 22:32:39 UTC |
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Primary ID | FDB023116 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Guanidinosuccinic acid |
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Description | Guanidinosuccinic acid (GSA) is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806) [HMDB] |
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CAS Number | 6133-30-8 |
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Structure | |
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Synonyms | Synonym | Source |
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(2S)-2-Carbamimidamidobutanedioic acid | ChEBI | L-N-Amidinoaspartic acid | ChEBI | N-(Aminoiminomethyl)-L-aspartic acid | ChEBI | N-Amidino-L-aspartic acid | Kegg | (2S)-2-Carbamimidamidobutanedioate | Generator | L-N-Amidinoaspartate | Generator | N-(Aminoiminomethyl)-L-aspartate | Generator | N-Amidino-L-aspartate | Generator | Guanidinosuccinate | Generator | N-Carbamimidoyl-L-aspartic acid | HMDB | Guanidinosuccinic acid, (DL)-isomer | MeSH, HMDB | Guanidinosuccinic acid | ChEBI | L-N-amidinoaspartic acid | hmdb | N-(aminoiminomethyl)-L-aspartic acid | hmdb | N-amidino-L-aspartic acid | hmdb | N-carbamimidoyl-L-aspartic acid | hmdb |
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Predicted Properties | |
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Chemical Formula | C5H9N3O4 |
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IUPAC name | (2S)-2-carbamimidamidobutanedioic acid |
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InChI Identifier | InChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1 |
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InChI Key | VVHOUVWJCQOYGG-REOHCLBHSA-N |
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Isomeric SMILES | NC(=N)N[C@@H](CC(O)=O)C(O)=O |
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Average Molecular Weight | 175.1427 |
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Monoisotopic Molecular Weight | 175.059305791 |
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Classification |
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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
- Guanidine
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Carboxylic acid
- Organopnictogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Carbonyl group
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Guanidinosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000x-9600000000-6898be602fa231388ab5 | Spectrum | Predicted GC-MS | Guanidinosuccinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9282000000-37ec05543d3d8d30ad15 | Spectrum | Predicted GC-MS | Guanidinosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-1900000000-466615ceb5129f085333 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-e5868bbf32c1407fa030 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-006x-9000000000-f34cd801b9c1e714a6fc | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9200000000-2cad41f1508b5f26c3a4 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0079-9100000000-05168c0ae4e3fdabfb73 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-004i-3900000000-df5df4302173fb4e9d29 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-001r-5900000000-a31472885115c0129885 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-36781515ea42c79fcca5 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-005i-5900000000-37fe8d8d0c84140e147c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-ba089dcdaa7d9545ac43 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-005i-2900000000-d58d2731ca71e2359e24 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-005i-3900000000-e366d1ed9f73879bd47f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-49e8a9df2b750e494685 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0a4r-9000000000-948b748bb9ac50e676a1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00dr-9100000000-ac4c3bddfe7b0a568fff | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-2900000000-e7544c898162e6c51b54 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-3900000000-f755abe1d2fcfc810e3f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0079-9200000000-78e26e891d49a63dc6b6 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-766bed5b22ec642474b7 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-090r-6900000000-c59abb9d78dd85396ad9 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9000000000-809ece24ff681a989230 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0089-1900000000-ab305bd5f1306019d2bb | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a5i-9500000000-e46a9bb7a8167700416d | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-cf381fa0309c6e1df17d | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-02a9-6900000000-3e4021155970f30bc06c | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 388951 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C03139 |
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Pubchem Compound ID | 439918 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17072 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03157 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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