Record Information |
---|
Version | 2.0 |
---|
Created at | 2006-08-12 20:28:49 UTC |
---|
Updated at | 2021-08-19 23:59:03 UTC |
---|
NP-MRD ID | NP0001336 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | D-Arginine |
---|
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). 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, the amino group is protonated, 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. D-Arginine is an essential amino acid that is physiologically active in the L-form. |
---|
Structure | 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 |
---|
Synonyms | Value | Source |
---|
(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 |
|
---|
Chemical Formula | C6H14N4O2 |
---|
Average Mass | 174.2010 Da |
---|
Monoisotopic Mass | 174.11168 Da |
---|
IUPAC Name | (2R)-2-amino-5-carbamimidamidopentanoic acid |
---|
Traditional Name | D-arginine |
---|
CAS Registry Number | 157-06-2 |
---|
SMILES | N[C@H](CCCNC(N)=N)C(O)=O |
---|
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 |
---|
InChI Key | ODKSFYDXXFIFQN-SCSAIBSYSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | 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 |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | D-alpha-amino acids |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | |
---|
Predicted Properties | |
---|
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 ]
- 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 ]
|
---|