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NG,NG-Dimethyl-L-arginine (FDB000508)

Record Information
Version1.0
Creation date2010-04-08 22:04:36 UTC
Update date2024-11-29 22:25:43 UTC
Primary IDFDB000508
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNG,NG-Dimethyl-L-arginine
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 found, on average, in the highest concentration within a few different foods, such as wheats, barley, and oats and in a lower concentration in romaine lettuces, turnips, and yellow bell peppers. Asymmetric dimethylarginine has also been detected, but not quantified in, pulses. This could make asymmetric dimethylarginine a potential biomarker for the consumption of these foods. Asymmetric dimethylarginine is a potentially toxic compound.
CAS Number30315-93-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H18N4O2
IUPAC name(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid
InChI IdentifierInChI=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
Isomeric SMILESN[C@@H](CCC\N=C(/N)N(C)C)C(O)=O
Average Molecular Weight202.2541
Monoisotopic Molecular Weight202.14297584
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 47.51%; H 8.97%; N 27.70%; O 15.82%DFC
Melting PointMp 198-201° (hydrochloride)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSNG,NG-Dimethyl-L-arginine, non-derivatized, GC-MS Spectrumsplash10-0f6w-1920000000-352e317361bed495b71bSpectrum
GC-MSNG,NG-Dimethyl-L-arginine, non-derivatized, GC-MS Spectrumsplash10-0f6w-1920000000-352e317361bed495b71bSpectrum
Predicted GC-MSNG,NG-Dimethyl-L-arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9300000000-4fc2a444d078a1eb4d85Spectrum
Predicted GC-MSNG,NG-Dimethyl-L-arginine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9520000000-928759e33b3f9821da4aSpectrum
Predicted GC-MSNG,NG-Dimethyl-L-arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNG,NG-Dimethyl-L-arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9100000000-2849c1945541be90da8a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9200000000-f7af59f4a85b35ee22392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-9310000000-901ceea58124eb646d2d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-1930000000-6a12bc30dbe08d316d092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-8900000000-47e0a5a868dce918c9b72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-d674ec18daa47f080be42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3390000000-2b624585e91010265a572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-9420000000-b8fe15104f41182b9d9b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9100000000-120212bd5d151152c8ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-9370000000-4bea91f4d0256a94739f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-2900000000-8fc254a7c96b0565c1ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-428e5ae3fbdfa34b338c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-2690000000-5766392f870c77d533592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9200000000-a7b438425f1f49a1a48b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-e6f7e053fa2072aa45ff2021-09-22View Spectrum
NMRNot Available
ChemSpider ID110375
ChEMBL IDCHEMBL457530
KEGG Compound IDC03626
Pubchem Compound ID123831
Pubchem Substance IDNot Available
ChEBI ID17929
Phenol-Explorer IDNot Available
DrugBank IDDB01686
HMDB IDHMDB01539
CRC / DFC (Dictionary of Food Compounds) IDBCZ64-N:BCZ65-O
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDA2
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAsymmetric dimethylarginine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
N(G),N(G)-dimethylarginine dimethylaminohydrolase 2DDAH2O95865
Pathways
NameSMPDB LinkKEGG Link
Metabolism and Phsyiological Effects of Asymmetric dimethylarginine (ADMA)SMP0124747 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference