Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:56:01 UTC
HMDB IDHMDB0001539
Secondary Accession Numbers
  • HMDB01539
Metabolite Identification
Common NameAsymmetric dimethylarginine
DescriptionAsymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. It is a metabolic by-product of continual protein modification processes in the cytoplasm of all human cells. It is closely related to L-arginine, a conditionally-essential amino acid. ADMA interferes with L-arginine in the production of nitric oxide, a key chemical to endothelial and hence cardiovascular health. Asymmetric dimethylarginine is created in protein methylation, a common mechanism of post-translational protein modification. This reaction is catalyzed by an enzyme set called S-adenosylmethionine protein N-methyltransferases (protein methylases I and II). The methyl groups transferred to create ADMA are derived from the methyl group donor S-adenosylmethionine, an intermediate in the metabolism of homocysteine. (Homocysteine is an important blood chemical, because it is also a marker of cardiovascular disease). After synthesis, ADMA migrates into the extracellular space and thence into blood plasma. Asymmetric dimethylarginine is measured using high performance liquid chromatography. ADMA has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Data?1676999746
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
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point195 - 197 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available147.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000092
[M+H]+Not Available143.615http://allccs.zhulab.cn/database/detail?ID=AllCCS00000092
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.52 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.71131661259
DarkChem[M-H]-146.42231661259
AllCCS[M+H]+146.97432859911
AllCCS[M-H]-146.7232859911
DeepCCS[M+H]+149.2630932474
DeepCCS[M-H]-146.90230932474
DeepCCS[M-2H]-182.02430932474
DeepCCS[M+Na]+157.03430932474
AllCCS[M+H]+147.032859911
AllCCS[M+H-H2O]+143.432859911
AllCCS[M+NH4]+150.332859911
AllCCS[M+Na]+151.232859911
AllCCS[M-H]-146.732859911
AllCCS[M+Na-2H]-148.032859911
AllCCS[M+HCOO]-149.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Asymmetric dimethylarginineN[C@@H](CCC\N=C(/N)N(C)C)C(O)=O2752.8Standard polar33892256
Asymmetric dimethylarginineN[C@@H](CCC\N=C(/N)N(C)C)C(O)=O1723.6Standard non polar33892256
Asymmetric dimethylarginineN[C@@H](CCC\N=C(/N)N(C)C)C(O)=O2237.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Asymmetric dimethylarginine,1TMS,isomer #1CN(C)/C(N)=N/CCC[C@H](N)C(=O)O[Si](C)(C)C1948.3Semi standard non polar33892256
Asymmetric dimethylarginine,1TMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O2065.9Semi standard non polar33892256
Asymmetric dimethylarginine,1TMS,isomer #3CN(C)/C(=N/CCC[C@H](N)C(=O)O)N[Si](C)(C)C2070.2Semi standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #1CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N[Si](C)(C)C2015.0Semi standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #1CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N[Si](C)(C)C1856.0Standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #1CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N[Si](C)(C)C3352.1Standard polar33892256
Asymmetric dimethylarginine,2TMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1987.5Semi standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1862.0Standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C3456.2Standard polar33892256
Asymmetric dimethylarginine,2TMS,isomer #3CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N[Si](C)(C)C2083.1Semi standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #3CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N[Si](C)(C)C1838.2Standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #3CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N[Si](C)(C)C3286.5Standard polar33892256
Asymmetric dimethylarginine,2TMS,isomer #4CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2122.2Semi standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #4CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1973.5Standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #4CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3609.1Standard polar33892256
Asymmetric dimethylarginine,2TMS,isomer #5CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2098.1Semi standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #5CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1958.9Standard non polar33892256
Asymmetric dimethylarginine,2TMS,isomer #5CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3554.1Standard polar33892256
Asymmetric dimethylarginine,3TMS,isomer #1CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C2066.2Semi standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #1CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C1903.6Standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #1CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C2882.7Standard polar33892256
Asymmetric dimethylarginine,3TMS,isomer #2CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2061.0Semi standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #2CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2035.3Standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #2CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3010.2Standard polar33892256
Asymmetric dimethylarginine,3TMS,isomer #3CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2122.3Semi standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #3CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2012.5Standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #3CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C3382.2Standard polar33892256
Asymmetric dimethylarginine,3TMS,isomer #4CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2191.9Semi standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #4CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C1982.4Standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #4CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C3002.2Standard polar33892256
Asymmetric dimethylarginine,3TMS,isomer #5CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2131.8Semi standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #5CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2033.5Standard non polar33892256
Asymmetric dimethylarginine,3TMS,isomer #5CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2837.2Standard polar33892256
Asymmetric dimethylarginine,4TMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2197.1Semi standard non polar33892256
Asymmetric dimethylarginine,4TMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2008.5Standard non polar33892256
Asymmetric dimethylarginine,4TMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C2704.0Standard polar33892256
Asymmetric dimethylarginine,4TMS,isomer #2CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2126.1Semi standard non polar33892256
Asymmetric dimethylarginine,4TMS,isomer #2CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2061.6Standard non polar33892256
Asymmetric dimethylarginine,4TMS,isomer #2CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2486.9Standard polar33892256
Asymmetric dimethylarginine,4TMS,isomer #3CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2225.3Semi standard non polar33892256
Asymmetric dimethylarginine,4TMS,isomer #3CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2158.9Standard non polar33892256
Asymmetric dimethylarginine,4TMS,isomer #3CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2609.0Standard polar33892256
Asymmetric dimethylarginine,5TMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2296.3Semi standard non polar33892256
Asymmetric dimethylarginine,5TMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2156.7Standard non polar33892256
Asymmetric dimethylarginine,5TMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2378.1Standard polar33892256
Asymmetric dimethylarginine,1TBDMS,isomer #1CN(C)/C(N)=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2142.3Semi standard non polar33892256
Asymmetric dimethylarginine,1TBDMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2265.0Semi standard non polar33892256
Asymmetric dimethylarginine,1TBDMS,isomer #3CN(C)/C(=N/CCC[C@H](N)C(=O)O)N[Si](C)(C)C(C)(C)C2285.0Semi standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #1CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2408.8Semi standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #1CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2240.4Standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #1CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3315.5Standard polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2379.2Semi standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2298.0Standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #2CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3501.2Standard polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #3CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N[Si](C)(C)C(C)(C)C2514.6Semi standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #3CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N[Si](C)(C)C(C)(C)C2225.6Standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #3CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N[Si](C)(C)C(C)(C)C3196.9Standard polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #4CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2528.1Semi standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #4CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2393.3Standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #4CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3599.5Standard polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #5CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2496.2Semi standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #5CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2368.9Standard non polar33892256
Asymmetric dimethylarginine,2TBDMS,isomer #5CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3384.2Standard polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #1CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2666.4Semi standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #1CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2441.0Standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #1CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2967.2Standard polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #2CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2656.6Semi standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #2CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2590.6Standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #2CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3046.1Standard polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #3CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2749.0Semi standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #3CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2624.3Standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #3CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3454.9Standard polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #4CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2801.9Semi standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #4CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2530.4Standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #4CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3043.0Standard polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #5CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2743.3Semi standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #5CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2593.5Standard non polar33892256
Asymmetric dimethylarginine,3TBDMS,isomer #5CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2922.7Standard polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3024.5Semi standard non polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2709.7Standard non polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2944.6Standard polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #2CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2910.8Semi standard non polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #2CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2754.9Standard non polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #2CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2805.1Standard polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #3CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3045.8Semi standard non polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #3CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2855.9Standard non polar33892256
Asymmetric dimethylarginine,4TBDMS,isomer #3CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2859.8Standard polar33892256
Asymmetric dimethylarginine,5TBDMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3246.4Semi standard non polar33892256
Asymmetric dimethylarginine,5TBDMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3004.4Standard non polar33892256
Asymmetric dimethylarginine,5TBDMS,isomer #1CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2792.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Asymmetric dimethylarginine GC-EI-TOF (Non-derivatized)splash10-0f6w-1920000000-352e317361bed495b71b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Asymmetric dimethylarginine GC-EI-TOF (Non-derivatized)splash10-0f6w-1920000000-352e317361bed495b71b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asymmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-4fc2a444d078a1eb4d852016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asymmetric dimethylarginine GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9520000000-928759e33b3f9821da4a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asymmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asymmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Asymmetric dimethylarginine 35V, Negative-QTOFsplash10-0006-9100000000-2849c1945541be90da8a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Asymmetric dimethylarginine 35V, Positive-QTOFsplash10-00di-9200000000-f7af59f4a85b35ee22392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Asymmetric dimethylarginine 35V, Positive-QTOFsplash10-00di-9310000000-901ceea58124eb646d2d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Positive-QTOFsplash10-0pbi-1930000000-6a12bc30dbe08d316d092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Positive-QTOFsplash10-0abi-8900000000-47e0a5a868dce918c9b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Positive-QTOFsplash10-00di-9000000000-d674ec18daa47f080be42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Negative-QTOFsplash10-0udi-3390000000-2b624585e91010265a572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Negative-QTOFsplash10-0f79-9420000000-b8fe15104f41182b9d9b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Negative-QTOFsplash10-00dl-9100000000-120212bd5d151152c8ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Negative-QTOFsplash10-0uk9-9370000000-4bea91f4d0256a94739f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Negative-QTOFsplash10-01si-2900000000-8fc254a7c96b0565c1ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Negative-QTOFsplash10-0006-9200000000-428e5ae3fbdfa34b338c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Positive-QTOFsplash10-0udr-2690000000-5766392f870c77d533592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Positive-QTOFsplash10-00dr-9200000000-a7b438425f1f49a1a48b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Positive-QTOFsplash10-00di-9000000000-e6f7e053fa2072aa45ff2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.30-1.00 uMAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.61 +/- 0.13 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.595 +/- 0.129 uMChildren (1-13 years old)MaleNormal details
BloodDetected and Quantified<0.30 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.35 (0.28-0.42) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.88(0.72-1.03) uMChildren (1-13 uears old)Both
Normal
details
BloodDetected and Quantified0989 +/- 0.297 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.45 +/- 0.11 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.66 +/- 0.04 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.06 +/- 0.008 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.13 +/- 0.074 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified8.86 +/- 12.1 umol/mmol creatinineChildren (1-13 years old)MaleNormal details
UrineDetected and Quantified2.92 +/- 0.42 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.98-4.87 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified2.34 +/- 0.52 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified2.3 +/- 0.97 umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified4.6 (3.00-7.00) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified15.2 +/- 3.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.7 (1.4-4.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.0 (0.2-6.7) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.76 (4.47-7.58) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.35 +/- 0.19 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified0.60 +/- 0.14 uMAdult (>18 years old)BothParkinson’s disease details
BloodDetected and Quantified0.60 +/- 0.14 uMAdult (>18 years old)BothParkinson’s disease with motor fluctuation details
BloodDetected and Quantified0.60 +/- 0.14 uMAdult (>18 years old)BothParkinson’s disease without motor fluctuation details
BloodDetected and Quantified0.631 +/- 0.119 uMChildren (1-13 years old)MaleDuchenne Muscular Dystrophy details
BloodDetected and Quantified2.40 (1.30-3.50) uMAdult (>18 years old)BothEssential hypertension details
BloodDetected and Quantified0.92(0.75-1.13) uMChildren (1-13 uears old)Both
Environmental enteric dysfunction
details
BloodDetected and Quantified0.00792 +/- 0.00594 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.91 +/- 0.04 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified1.04 +/- 0.04 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified0.87 +/- 0.04 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified0.97 +/- 0.02 uMAdult (>18 years old)Both
Kidney disease
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.11 +/- 0.049 uMAdult (>18 years old)BothParkinson’s disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.12 +/- 0.033 uMAdult (>18 years old)BothParkinson’s disease with motor fluctuation details
Cerebrospinal Fluid (CSF)Detected and Quantified0.072 +/- 0.019 uMAdult (>18 years old)BothParkinson’s disease without motor fluctuation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified20.3 +/- 10.2 umol/mmol creatinineChildren (1-13 years old)MaleDuchenne Muscular Dystrophy details
UrineDetected and Quantified22.0 +/- 4.0 umol/mmol creatinineAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Essential hypertension
  1. Surdacki A, Nowicki M, Sandmann J, Tsikas D, Boeger RH, Bode-Boeger SM, Kruszelnicka-Kwiatkowska O, Kokot F, Dubiel JS, Froelich JC: Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension. J Cardiovasc Pharmacol. 1999 Apr;33(4):652-8. [PubMed:10218738 ]
Kidney disease
  1. Fleck C, Schweitzer F, Karge E, Busch M, Stein G: Serum concentrations of asymmetric (ADMA) and symmetric (SDMA) dimethylarginine in patients with chronic kidney diseases. Clin Chim Acta. 2003 Oct;336(1-2):1-12. [PubMed:14500028 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Duchenne Muscular Dystrophy
  1. Horster I, Weigt-Usinger K, Carmann C, Chobanyan-Jurgens K, Kohler C, Schara U, Kayacelebi AA, Beckmann B, Tsikas D, Lucke T: The L-arginine/NO pathway and homoarginine are altered in Duchenne muscular dystrophy and improved by glucocorticoids. Amino Acids. 2015 Sep;47(9):1853-63. doi: 10.1007/s00726-015-2018-x. Epub 2015 Jun 12. [PubMed:26066683 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Autosomal dominant polycystic kidney disease
  1. Wang D, Strandgaard S, Borresen ML, Luo Z, Connors SG, Yan Q, Wilcox CS: Asymmetric dimethylarginine and lipid peroxidation products in early autosomal dominant polycystic kidney disease. Am J Kidney Dis. 2008 Feb;51(2):184-91. doi: 10.1053/j.ajkd.2007.09.020. [PubMed:18215696 ]
Associated OMIM IDs
  • 310200 (Duchenne Muscular Dystrophy)
  • 114500 (Colorectal cancer)
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDDB01686
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDDMLARG
MarkerDB IDMDB00013441
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. van Guldener C, Nanayakkara PW, Stehouwer CD: Homocysteine and asymmetric dimethylarginine (ADMA): biochemically linked but differently related to vascular disease in chronic kidney disease. Clin Chem Lab Med. 2007;45(12):1683-7. [PubMed:17937610 ]
  2. Surdacki A, Nowicki M, Sandmann J, Tsikas D, Boeger RH, Bode-Boeger SM, Kruszelnicka-Kwiatkowska O, Kokot F, Dubiel JS, Froelich JC: Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension. J Cardiovasc Pharmacol. 1999 Apr;33(4):652-8. [PubMed:10218738 ]
  3. Martens-Lobenhoffer J, Bode-Boger SM: Measurement of asymmetric dimethylarginine (ADMA) in human plasma: from liquid chromatography estimation to liquid chromatography-mass spectrometry quantification. Eur J Clin Pharmacol. 2006 Feb;62(Supplement 13):61-68. [PubMed:16217682 ]
  4. Watanabe T, Kato S, Sato K, Nagata K: Nitric oxide regulation system in degenerative lumbar disease. Kurume Med J. 2005;52(1-2):39-47. [PubMed:16119611 ]
  5. Nijveldt RJ, Teerlink T, Siroen MP, van der Hoven B, Prins HA, Wiezer MJ, Meijer C, van der Sijp JR, Cuesta MA, Meijer S, van Leeuwen PA: Elevation of asymmetric dimethylarginine (ADMA) in patients developing hepatic failure after major hepatectomy. JPEN J Parenter Enteral Nutr. 2004 Nov-Dec;28(6):382-7. [PubMed:15568284 ]
  6. Siroen MP, Warle MC, Teerlink T, Nijveldt RJ, Kuipers EJ, Metselaar HJ, Tilanus HW, Kuik DJ, van der Sijp JR, Meijer S, van der Hoven B, van Leeuwen PA: The transplanted liver graft is capable of clearing asymmetric dimethylarginine. Liver Transpl. 2004 Dec;10(12):1524-30. [PubMed:15558588 ]
  7. Tarnow L, Hovind P, Teerlink T, Stehouwer CD, Parving HH: Elevated plasma asymmetric dimethylarginine as a marker of cardiovascular morbidity in early diabetic nephropathy in type 1 diabetes. Diabetes Care. 2004 Mar;27(3):765-9. [PubMed:14988299 ]
  8. Wang J, Sim AS, Wang XL, Salonikas C, Naidoo D, Wilcken DE: Relations between plasma asymmetric dimethylarginine (ADMA) and risk factors for coronary disease. Atherosclerosis. 2006 Feb;184(2):383-8. Epub 2005 Jun 6. [PubMed:15939423 ]
  9. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  10. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:
DDAH1
Uniprot ID:
O94760
Molecular weight:
20189.135
Reactions
Asymmetric dimethylarginine + Water → Dimethylamine + Citrullinedetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:
DDAH2
Uniprot ID:
O95865
Molecular weight:
29643.54
Reactions
Asymmetric dimethylarginine + Water → Dimethylamine + Citrullinedetails
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
References
  1. van Guldener C, Nanayakkara PW, Stehouwer CD: Homocysteine and asymmetric dimethylarginine (ADMA): biochemically linked but differently related to vascular disease in chronic kidney disease. Clin Chem Lab Med. 2007;45(12):1683-7. [PubMed:17937610 ]
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets. Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
Gene Name:
NOS3
Uniprot ID:
P29474
Molecular weight:
133273.59
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]