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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-13 22:26:44 UTC |
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Update Date | 2020-10-09 21:10:43 UTC |
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HMDB ID | HMDB0004620 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-a-Acetyl-L-arginine |
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Description | N-a-Acetyl-L-arginine, also known as N-ac-L-arg-OH or N-alpha-acetylarginine, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-a-Acetyl-L-arginine serum levels (and other guanidino compounds) were elevated of all the hyperargininemic patients are higher than the normal range. N-a-Acetyl-L-arginine is a very strong basic compound (based on its pKa). Untreated hyperargininemic patients have the highest guanidino compound levels in cerebrospinal fluid. N-a-Acetyl-L-arginine is one of the guanidino compounds found elevated in the serum of an hemodialyzed renal insufficient (uremic) pediatric population. Outside of the human body, N-a-Acetyl-L-arginine has been detected, but not quantified in, apples and loquats. This could make N-a-acetyl-L-arginine a potential biomarker for the consumption of these foods. N-a-Acetyl-L-arginine, with regard to humans, has been found to be associated with several diseases such as uremia and colorectal cancer; N-a-acetyl-L-arginine has also been linked to the inborn metabolic disorder hyperargininemia. During a low-arginine diet, together with sodium benzoate therapy, there was a marked decrease in plasma N-alpha-acetylarginine. N-a-Acetyl-L-arginine increases in urine hyperargininemic patients. |
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Structure | |
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Synonyms | Value | Source |
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N-Ac-L-arg-OH | ChEBI | N-Acetyl-L-arginine | ChEBI | N(2)-Acetyl-L-arginine | ChEBI | N-alpha-Acetyl-L-arginine | HMDB | N-alpha-L-Acetyl-arginine | HMDB | N2-Acetyl-L-arginine | HMDB | Acetyl arginine | HMDB | N-alpha-Acetylarginine | HMDB | N(a)-Acetyl-L-arginine | HMDB | N(Α)-acetyl-L-arginine | HMDB | N-a-L-Acetyl-arginine | Generator | N-Α-L-acetyl-arginine | Generator |
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Chemical Formula | C8H16N4O3 |
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Average Molecular Weight | 216.2376 |
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Monoisotopic Molecular Weight | 216.122240398 |
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IUPAC Name | (2S)-5-carbamimidamido-2-acetamidopentanoic acid |
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Traditional Name | N~2~-acetyl-L-arginine |
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CAS Registry Number | 155-84-0 |
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SMILES | CC(=O)N[C@@H](CCCNC(N)=N)C(O)=O |
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InChI Identifier | InChI=1S/C8H16N4O3/c1-5(13)12-6(7(14)15)3-2-4-11-8(9)10/h6H,2-4H2,1H3,(H,12,13)(H,14,15)(H4,9,10,11)/t6-/m0/s1 |
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InChI Key | SNEIUMQYRCDYCH-LURJTMIESA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. |
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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 | N-acyl-L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-l-alpha-amino acid
- Fatty acid
- Acetamide
- Carboxamide group
- Guanidine
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carboximidamide
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Organic nitrogen compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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: Biological location: Source: |
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Role | Industrial application: |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-006x-9300000000-1ceaef8ce37a7b0824d7 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-006x-9520000000-c079d35b9012a55883d2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01b9-1940000000-495d7eb88df38bf7a81f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03mi-2900000000-a1ce241787b062182472 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9400000000-d6685c90df9e6a8f2a03 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00xr-2930000000-c8a853d3dffa744063ac | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0adi-4900000000-99f3a540de4819b0d14e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9100000000-e57d664a81b0164998d5 | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 1.25 +/- 0.28 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.0838 +/- 0.115 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.15 (0.07-0.23) uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 1.38 (0.64-2.12) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 1.520 +/- 0.660 uM | Adult (>18 years old) | Both | Uremia | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.5 (0.0-1.0) uM | Adult (>18 years old) | Not Specified | Hyperargininemia | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Uremia |
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- Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
| Hyperargininemia |
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- Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [PubMed:3433275 ]
| Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB01985 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023383 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 60752 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 67427 |
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PDB ID | Not Available |
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ChEBI ID | 40521 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00030009 |
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References |
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Synthesis Reference | Bergmann, Max; Koster, Hans. Rearrangements of peptide-like substances. XII. Arginine and its conversion into ornithino. Z. physiol. Chem. (1926), 159 179-89. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [PubMed:3433275 ]
- De Deyn PP, Robitaille P, Vanasse M, Qureshi IA, Marescau B: Serum guanidino compound levels in uremic pediatric patients treated with hemodialysis or continuous cycle peritoneal dialysis. Correlations between nerve conduction velocities and altered guanidino compound concentrations. Nephron. 1995;69(4):411-7. [PubMed:7777105 ]
- Marescau B, De Deyn PP, Lowenthal A, Qureshi IA, Antonozzi I, Bachmann C, Cederbaum SD, Cerone R, Chamoles N, Colombo JP, et al.: Guanidino compound analysis as a complementary diagnostic parameter for hyperargininemia: follow-up of guanidino compound levels during therapy. Pediatr Res. 1990 Mar;27(3):297-303. [PubMed:1690873 ]
- Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. [PubMed:3987036 ]
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