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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-12 20:28:49 UTC |
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Update Date | 2020-02-26 21:24:35 UTC |
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HMDB ID | HMDB0003416 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Arginine |
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Description | D-Arginine, also known as D-2-amino-5-guanidinovaleric acid or (2R)-2-amino-5-guanidinopentanoate, is a member of the class of compounds known as D-alpha-amino acids. D-alpha-Amino acids are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-Arginine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). D-Arginine can be found in human epidermis and platelet tissues. Within the cell, D-arginine is primarily located in the peroxisome. In humans, D-arginine is involved in D-arginine and D-ornithine metabolism. Arginine (abbreviated as Arg or R) is an alpha-amino acid that is used in the biosynthesis of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. It contains an alpha-amino group, an alpha-carboxylic acid group, and a side chain consisting of a 3-carbon aliphatic straight chain ending in a guanidino group. At physiological pH, the carboxylic acid is deprotonated (−COO−), the amino group is protonated (−NH3+), and the guanidino group is also protonated to give the guanidinium form (-C-(NH2)2+), making arginine a charged, aliphatic amino acid. It is the precursor for the biosynthesis of nitric oxide (Wikipedia ). D-Arginine is an essential amino acid that is physiologically active in the L-form. |
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Structure | |
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Synonyms | Value | Source |
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(2R)-2-Amino-5-(carbamimidamido)pentanoic acid | ChEBI | (2R)-2-Amino-5-guanidinopentanoic acid | ChEBI | (R)-2-Amino-5-guanidinopentanoic acid | ChEBI | D-2-Amino-5-guanidinovaleric acid | ChEBI | D-Arginin | ChEBI | DAR | ChEBI | (2R)-2-Amino-5-(carbamimidamido)pentanoate | Generator | (2R)-2-Amino-5-guanidinopentanoate | Generator | (R)-2-Amino-5-guanidinopentanoate | Generator | D-2-Amino-5-guanidinovalerate | Generator |
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Chemical Formula | C6H14N4O2 |
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Average Molecular Weight | 174.201 |
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Monoisotopic Molecular Weight | 174.111675712 |
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IUPAC Name | (2R)-2-amino-5-carbamimidamidopentanoic acid |
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Traditional Name | D-arginine |
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CAS Registry Number | 157-06-2 |
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SMILES | N[C@H](CCCNC(N)=N)C(O)=O |
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InChI Identifier | InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1 |
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InChI Key | ODKSFYDXXFIFQN-SCSAIBSYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-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 | D-alpha-amino acids |
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Alternative Parents | |
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Substituents | - D-alpha-amino acid
- Fatty acid
- Guanidine
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carboximidamide
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Amine
- Hydrocarbon derivative
- Organic oxide
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- 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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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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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 | splash10-00dl-9100000000-60db59de76b9a9b5bfc8 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00dl-9510000000-a5f3be057956f5efb0fd | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-1900000000-a1207a353a5d383e8118 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-38faac95afc81e981a08 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-776b9e0f6bf6a0ddf5ba | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-1900000000-0627028bdd33e89ac545 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03mi-8900000000-d00d08306af5359ec3dc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9000000000-09fdbc63550a3fe95638 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00e9-2900000000-4f23a56d70e700301134 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-053r-7900000000-02e7df28226010832ffe | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-435f29993f2aaceb0d44 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB04027 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023167 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 64224 |
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KEGG Compound ID | C00792 |
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BioCyc ID | CPD-220 |
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BiGG ID | 36012 |
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Wikipedia Link | Arginine |
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METLIN ID | 6924 |
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PubChem Compound | 71070 |
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PDB ID | Not Available |
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ChEBI ID | 15816 |
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Food Biomarker Ontology | Not Available |
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VMH ID | ARG_D |
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MarkerDB ID | |
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References |
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Synthesis Reference | Birnbaum, Sanford M.; Winitz, Milton; Greenstein, Jesse P. A simplified preparation of D-arginine. Archives of Biochemistry and Biophysics (1956), 60 496-8. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Hensel RR, King RC, Owens KG: Electrospray sample preparation for improved quantitation in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 1997;11(16):1785-93. [PubMed:9375412 ]
- Svedman P, Lundin S, Svedman C: Administration of antidiuretic peptide (DDAVP) by way of suction de-epithelialised skin. Lancet. 1991 Jun 22;337(8756):1506-9. [PubMed:1675370 ]
- Tulandi T, Yusuf N, Posner BI: Diabetes insipidus: a postpartum complication. Obstet Gynecol. 1987 Sep;70(3 Pt 2):492-5. [PubMed:3498136 ]
- van Lieburg AF, Verdijk MA, Schoute F, Ligtenberg MJ, van Oost BA, Waldhauser F, Dobner M, Monnens LA, Knoers NV: Clinical phenotype of nephrogenic diabetes insipidus in females heterozygous for a vasopressin type 2 receptor mutation. Hum Genet. 1995 Jul;96(1):70-8. [PubMed:7607658 ]
- Sorensen PS, Vilhardt H, Gjerris F, Warberg J: Impermeability of the blood-cerebrospinal fluid barrier to 1-deamino-8-D-arginine-vasopressin (DDAVP) in patients with acquired, communicating hydrocephalus. Eur J Clin Invest. 1984 Dec;14(6):435-9. [PubMed:6441719 ]
- Casonato A, Sartorello F, Cattini MG, Pontara E, Soldera C, Bertomoro A, Girolami A: An Arg760Cys mutation in the consensus sequence of the von Willebrand factor propeptide cleavage site is responsible for a new von Willebrand disease variant. Blood. 2003 Jan 1;101(1):151-6. Epub 2002 Aug 8. [PubMed:12393698 ]
- Ross MG, Cedars L, Nijland MJ, Ogundipe A: Treatment of oligohydramnios with maternal 1-deamino-[8-D-arginine] vasopressin-induced plasma hypoosmolality. Am J Obstet Gynecol. 1996 May;174(5):1608-13. [PubMed:9065138 ]
- Hochreutener H, Issakainen J, Bachmann C, Baerlocher K: [Carbamyl phosphate synthase deficiency: clinical symptoms, diagnosis and dietary-medicamentous treatment in the neonatal period and infancy]. Helv Paediatr Acta. 1989 Jun;43(5-6):493-505. [PubMed:2745145 ]
- Abiko T, Sekino H: Synthesis of an immunologically active fragment analog of prothymosin alpha with enhanced enzymatic stability. Chem Pharm Bull (Tokyo). 1991 Mar;39(3):752-6. [PubMed:2070460 ]
- Ritchie JL, Alexander HD, Allen P, Morgan D, McVeigh GE: Effect of nitric oxide modulation on systemic haemodynamics and platelet activation determined by P-selectin expression. Br J Haematol. 2002 Mar;116(4):892-8. [PubMed:11886397 ]
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