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Record Information
Version3.6
Creation Date2006-08-10 09:50:09 UTC
Update Date2016-02-11 01:06:10 UTC
HMDB IDHMDB03334
Secondary Accession NumbersNone
Metabolite Identification
Common NameSymmetric dimethylarginine
DescriptionSymmetric dimethylarginine (SDMA) is an endogenously produced inhibitor of nitric oxide synthase (EC-Number 1.14.13.39). However, elevated levels of SDMA occur in patients with vascular disease, especially suffering end-stage renal disease. (PMID 12401860 ).
Structure
Thumb
Synonyms
ValueSource
guanidino-N(1),N(2)-DimethylarginineHMDB
N(g1),N(g2)-DimethylarginineHMDB
N,N'-dimethylarginineHMDB
N5-((methylamino)(methylimino)Methyl)-L-ornithineHMDB
N5-(N,N'-dimethylamidino)-L-ornithineHMDB
N5-[Bis(methylamino)methylene]-L-ornithineHMDB
NG,N'G-dimethyl-L-arginineHMDB
NG,N'G-dimethylarginineHMDB
NG,NG'-dimethylarginineHMDB
SDMAHMDB
Chemical FormulaC8H18N4O2
Average Molecular Weight202.2541
Monoisotopic Molecular Weight202.14297584
IUPAC Name(2S)-2-amino-5-[(E)-2,3-dimethylcarbamimidamido]pentanoic acid
Traditional NameN3, N4-dimethylarginine
CAS Registry Number30344-00-4
SMILES
CN\C(NCCC[C@H](N)C(O)=O)=N/C
InChI Identifier
InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1
InChI KeyInChIKey=HVPFXCBJHIIJGS-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.56 mg/mLALOGPS
logP-2.9ALOGPS
logP-2.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)12.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.74 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.18 m3·mol-1ChemAxon
Polarizability22.22 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Kidney
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.460 (0.368-0.552) uMAdult (>18 years old)BothNormal
    • Martens-Lobenhoff...
details
BloodDetected and Quantified0.49 +/- 0.03 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.678 +/- 0.037 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.38 +/- 0.10 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.46 (0.368-0.552) uMAdult (>18 years old)Not SpecifiedNormal
    • Martens-Lobenhoff...
details
SalivaDetected and Quantified0.35 +/- 0.20 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified3.72 +/- 0.35 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified4.6 (3.5-7.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified20.2 +/- 8.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.8 (2.0-9.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.7 (1.5-5.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.08 +/- 0.11 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified3.19 +/- 2.97 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified2.69 +/- 0.12 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified2.28 +/- 0.13 uMAdult (>18 years old)Not Specified
Kidney disease
details
BloodDetected and Quantified1.41 +/- 0.10 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified2.19 +/- 0.16 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified2.87 +/- 0.15 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified2.15 +/- 0.15 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified2.12 +/- 0.09 uMAdult (>18 years old)Both
Kidney disease
details
UrineDetected and Quantified22.0 +/- 8.0 umol/mmol creatinineAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
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. [18215696 ]
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. [14500028 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDDB02302
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000509
KNApSAcK IDNot Available
Chemspider ID147942
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSDMA
NuGOwiki LinkHMDB03334
Metagene LinkHMDB03334
METLIN ID6891
PubChem Compound169148
PDB ID2MR
ChEBI ID61914
References
Synthesis ReferenceZinellu Angelo; Sotgia Salvatore; Scanu Bastianina; Formato Marilena; Deiana Luca; Carru Ciriaco Assessment of protein-incorporated arginine methylation in biological specimens by CZE UV-detection. Electrophoresis (2007), 28(23), 4452-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [16217682 ]
  2. 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. [15939423 ]
  3. 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. [14500028 ]
  4. Boger RH, Bode-Boger SM, Szuba A, Tsao PS, Chan JR, Tangphao O, Blaschke TF, Cooke JP: Asymmetric dimethylarginine (ADMA): a novel risk factor for endothelial dysfunction: its role in hypercholesterolemia. Circulation. 1998 Nov 3;98(18):1842-7. [9799202 ]
  5. Nijveldt RJ, Van Leeuwen PA, Van Guldener C, Stehouwer CD, Rauwerda JA, Teerlink T: Net renal extraction of asymmetrical (ADMA) and symmetrical (SDMA) dimethylarginine in fasting humans. Nephrol Dial Transplant. 2002 Nov;17(11):1999-2002. [12401860 ]
  6. Schiel R, Franke S, Busch M, Muller A, Fleck C, Muller UA, Braun A, Stein G: Effect of smoking on risk factors for cardiovascular disease in patients with diabetes mellitus and renal insufficiency. Eur J Med Res. 2003 Jul 31;8(7):283-91. [12911864 ]
  7. Mittermayer F, Pleiner J, Krzyzanowska K, Wiesinger GF, Francesconi M, Wolzt M: Regular physical exercise normalizes elevated asymmetrical dimethylarginine concentrations in patients with type 1 diabetes mellitus. Wien Klin Wochenschr. 2005 Dec;117(23-24):816-20. [16437318 ]
  8. Krzyzanowska K, Mittermayer F, Schnack C, Hofer M, Wolzt M, Schernthaner G: Circulating ADMA concentrations are elevated in hypopituitary adults with and without growth hormone deficiency. Eur J Clin Invest. 2005 Mar;35(3):208-13. [15733076 ]
  9. Marliss EB, Chevalier S, Gougeon R, Morais JA, Lamarche M, Adegoke OA, Wu G: Elevations of plasma methylarginines in obesity and ageing are related to insulin sensitivity and rates of protein turnover. Diabetologia. 2006 Feb;49(2):351-9. Epub 2005 Dec 21. [16369774 ]
  10. Schmidt RJ, Baylis C: Total nitric oxide production is low in patients with chronic renal disease. Kidney Int. 2000 Sep;58(3):1261-6. [10972689 ]
  11. Ellis J, Wennerholm UB, Bengtsson A, Lilja H, Pettersson A, Sultan B, Wennergren M, Hagberg H: Levels of dimethylarginines and cytokines in mild and severe preeclampsia. Acta Obstet Gynecol Scand. 2001 Jul;80(7):602-8. [11437716 ]
  12. Teerlink T, Neele SJ, de Jong S, Netelenbos JC, Stehouwer CD: Oestrogen replacement therapy lowers plasma levels of asymmetrical dimethylarginine in healthy postmenopausal women. Clin Sci (Lond). 2003 Jul;105(1):67-71. [12625833 ]
  13. Mittermayer F, Namiranian K, Pleiner J, Schaller G, Wolzt M: Acute Escherichia coli endotoxaemia decreases the plasma l-arginine/asymmetrical dimethylarginine ratio in humans. Clin Sci (Lond). 2004 Jun;106(6):577-81. [14741043 ]