Identification
YMDB IDYMDB01554
NameDimethyl-L-arginine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionAsymmetric dimethylarginine, also known as N(g),N(g)-dimethylarginine or ADMA, belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Asymmetric dimethylarginine is a very strong basic compound (based on its pKa). Asymmetric dimethylarginine exists in all eukaryotes, ranging from yeast to humans. Asymmetric dimethylarginine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-amino-5-(amino-dimethylamino-Methylidene)amino-pentanoate
  • 2-amino-5-(amino-dimethylamino-Methylidene)amino-pentanoic acid
  • ADMA
  • Asymmetric dimethylarginine
  • Dimethyl-L-arginine
  • guanidino-N,N-Dimethylarginine
  • N(5)-((dimethylamino)Iminomethyl)-L-ornithine
  • N(g)-Dimethylarginine
  • N(g),N(g)-Dimethylarginine
  • N(g1),N(g1)-Dimethylarginine
  • N(Omega),N(omega)-dimethyl-L-arginine
  • NG-Dimethylarginine
  • NG,NG-Dimethyl-L-arginine
  • NG,NG-Dimethylarginine
  • Nomega,nomega'-dimethyl-L-arginine
  • N,N-Dimethylarginine
  • Nomega,nomega-dimethyl-L-arginine
CAS number102783-24-4
WeightAverage: 202.2541
Monoisotopic: 202.14297584
InChI KeyYDGMGEXADBMOMJ-LURJTMIESA-N
InChIInChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1
IUPAC Name(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid
Traditional IUPAC Nameasymmetric dimethylarginine
Chemical FormulaC8H18N4O2
SMILESCN(C)C(=N)NCCC[C@H](N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentArginine and derivatives
Alternative Parents
Substituents
  • Arginine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point195-197 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.77 g/LALOGPS
logP-3.1ALOGPS
logP-2.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)12.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.94 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.7 m³·mol⁻¹ChemAxon
Polarizability22.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
3 ± 0 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6w-1920000000-352e317361bed495b71bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6w-1920000000-352e317361bed495b71bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-4fc2a444d078a1eb4d85JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9520000000-928759e33b3f9821da4aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9100000000-2849c1945541be90da8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9200000000-f7af59f4a85b35ee2239JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9310000000-901ceea58124eb646d2dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-1930000000-6a12bc30dbe08d316d09JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-8900000000-47e0a5a868dce918c9b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-d674ec18daa47f080be4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3390000000-2b624585e91010265a57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-9420000000-b8fe15104f41182b9d9bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9100000000-120212bd5d151152c8adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-9370000000-4bea91f4d0256a94739fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-2900000000-8fc254a7c96b0565c1ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-428e5ae3fbdfa34b338cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-2690000000-5766392f870c77d53359JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9200000000-a7b438425f1f49a1a48bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-e6f7e053fa2072aa45ffJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17929
HMDB IDHMDB01539
Pubchem Compound ID123831
Kegg IDC03626
ChemSpider ID110375
FOODB IDFDB000508
Wikipedia IDAsymmetric dimethylarginine
BioCyc IDCPD-596