D-Arginine (CHEM035524)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:50:51 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035524
Identification
Common NameD-Arginine
ClassSmall Molecule
DescriptionA D-alpha-amino acid that is the D-isomer of arginine.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2-Amino-5-(carbamimidamido)pentanoic acidChEBI
(2R)-2-Amino-5-guanidinopentanoic acidChEBI
(R)-2-Amino-5-guanidinopentanoic acidChEBI
D-2-Amino-5-guanidinovaleric acidChEBI
D-ArgininChEBI
DARChEBI
(2R)-2-Amino-5-(carbamimidamido)pentanoateGenerator
(2R)-2-Amino-5-guanidinopentanoateGenerator
(R)-2-Amino-5-guanidinopentanoateGenerator
D-2-Amino-5-guanidinovalerateGenerator
Chemical FormulaC6H14N4O2
Average Molecular Mass174.201 g/mol
Monoisotopic Mass174.112 g/mol
CAS Registry Number157-06-2
IUPAC Name(2R)-2-amino-5-carbamimidamidopentanoic acid
Traditional NameD-arginine
SMILESN[C@H](CCCNC(N)=N)C(O)=O
InChI IdentifierInChI=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 KeyODKSFYDXXFIFQN-SCSAIBSYSA-N
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.28 g/LALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)12.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.92 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9100000000-60db59de76b9a9b5bfc8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9510000000-a5f3be057956f5efb0fdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-1900000000-a1207a353a5d383e8118Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-38faac95afc81e981a08Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-776b9e0f6bf6a0ddf5baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-0627028bdd33e89ac545Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03mi-8900000000-d00d08306af5359ec3dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-09fdbc63550a3fe95638Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-2900000000-4f23a56d70e700301134Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-7900000000-02e7df28226010832ffeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-435f29993f2aaceb0d44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-fe2cccae6934dad0053bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-da3c09ec6a806e5c0777Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-15e9d13a1d44b86b2a6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-a706f1985fb3e9e0adbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900000000-b42c24606ae24000888dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e43Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04027
HMDB IDHMDB0003416
FooDB IDFDB023167
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID36012
BioCyc IDCPD-220
METLIN ID6924
PDB IDNot Available
Wikipedia LinkArginine
Chemspider ID64224
ChEBI ID15816
PubChem Compound ID71070
Kegg Compound IDC00792
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15540275
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15723827
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16912865
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19651461
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22518022
6. Birnbaum, Sanford M.; Winitz, Milton; Greenstein, Jesse P. A simplified preparation of D-arginine. Archives of Biochemistry and Biophysics (1956), 60 496-8.
7. 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.
8. 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.
9. Tulandi T, Yusuf N, Posner BI: Diabetes insipidus: a postpartum complication. Obstet Gynecol. 1987 Sep;70(3 Pt 2):492-5.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.