Showing metabocard for Dimethyl-L-arginine (BMDB0001539)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:23 UTC
Update Date2020-06-04 19:39:56 UTC
MCDB ID BMDB0001539
Secondary Accession Numbers
  • BMDB01539
Metabolite Identification
Common NameDimethyl-L-arginine
DescriptionAsymmetric dimethylarginine, also known as N(g),N(g)-dimethylarginine or guanidino-N,N-dimethylarginine, 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Asymmetric dimethylarginine exists in all eukaryotes, ranging from yeast to humans. Asymmetric dimethylarginine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ADMAChEBI
Guanidino-N,N-dimethylarginineChEBI
N,N-DimethylarginineChEBI
N(5)-((Dimethylamino)iminomethyl)-L-ornithineChEBI
NG,NG-Dimethyl-L-arginineChEBI
N(g),N(g)-DimethylarginineChEBI
N(g)-DimethylarginineChEBI
N(g1),N(g1)-DimethylarginineChEBI
Nomega,nomega-dimethyl-L-arginineKegg
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoateHMDB
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acidHMDB
Dimethyl-L-arginineHMDB
N(Omega),N(omega)-dimethyl-L-arginineHMDB
NG,NG-DimethylarginineHMDB
NG-DimethylarginineHMDB
Nomega,nomega'-dimethyl-L-arginineHMDB
Asymmetric dimethylarginineChEBI
Chemical FormulaC8H18N4O2
Average Molecular Weight202.2541
Monoisotopic Molecular Weight202.14297584
IUPAC Name(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid
Traditional Nameasymmetric dimethylarginine
CAS Registry Number30315-93-6
SMILES
N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O
InChI Identifier
InChI=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
InChI KeyYDGMGEXADBMOMJ-LURJTMIESA-N
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
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6w-1920000000-352e317361bed495b71b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6w-1920000000-352e317361bed495b71b2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-4fc2a444d078a1eb4d852016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9520000000-928759e33b3f9821da4a2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9100000000-2849c1945541be90da8a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9200000000-f7af59f4a85b35ee22392021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9310000000-901ceea58124eb646d2d2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-1930000000-6a12bc30dbe08d316d092016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-8900000000-47e0a5a868dce918c9b72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-d674ec18daa47f080be42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3390000000-2b624585e91010265a572016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-9420000000-b8fe15104f41182b9d9b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9100000000-120212bd5d151152c8ad2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-9370000000-4bea91f4d0256a94739f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-2900000000-8fc254a7c96b0565c1ff2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-428e5ae3fbdfa34b338c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-2690000000-5766392f870c77d533592021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9200000000-a7b438425f1f49a1a48b2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-e6f7e053fa2072aa45ff2021-09-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.08 +/- 0.01 uM details
Detected and Quantified0.09 +/- 0.01 uM details
Detected and Quantified0.1 +/- 0.01 uM details
Detected and Quantified0.10 +/- 0.01 uM details
HMDB IDHMDB0001539
DrugBank IDDB01686
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000508
KNApSAcK IDNot Available
Chemspider ID110375
KEGG Compound IDC03626
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAsymmetric dimethylarginine
METLIN ID6309
PubChem Compound123831
PDB IDNot Available
ChEBI ID17929
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.