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Record Information
Version4.0
Creation Date2006-08-10 09:50:09 UTC
Update Date2017-09-27 08:24:20 UTC
HMDB IDHMDB0003334
Secondary Accession Numbers
  • HMDB03334
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
(2S)-2-amino-5-(N',n''-dimethylcarbamimidamido)pentanoic acidChEBI
(S)-2-amino-5-(N',n''-dimethylguanidino)pentanoic acidChEBI
guanidino-N(1),N(2)-DimethylarginineChEBI
N(g1),N(g2)-DimethylarginineChEBI
N,N'-dimethylarginineChEBI
N(3),N(4)-Dimethyl-L-arginineChEBI
N(3),N(4)-DimethylarginineChEBI
N5-((methylamino)(methylimino)Methyl)-L-ornithineChEBI
N(5)-(N,N'-dimethylamidino)-L-ornithineChEBI
N(5)-(N,N'-dimethylcarbamimidoyl)-L-ornithineChEBI
N(5)-[Bis(methylamino)methylene]-L-ornithineChEBI
N(g),N'(g)-dimethyl-L-arginineChEBI
N(g),N'(g)-dimethylarginineChEBI
SDMAChEBI
(2S)-2-amino-5-(N',n''-dimethylcarbamimidamido)pentanoateGenerator
(S)-2-amino-5-(N',n''-dimethylguanidino)pentanoateGenerator
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
Omega-N(g),n'(g)-dimethylarginineMeSH
SDMA arginineMeSH
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 KeyHVPFXCBJHIIJGS-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as arginine and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentArginine and derivatives
Alternative Parents
Substituents
  • Arginine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Imine
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    Psychiatric disorders:

    Renal and urinary disorders:

    Nervous system disorders:

  Observation:

    Investigations:

Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

Route of exposure:

  Parenteral:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.18 m³·mol⁻¹ChemAxon
Polarizability22.22 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfx-9600000000-f6c986d30ea287579a78View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fkc-9720000000-0f297fd1183458956770View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pbi-1930000000-98ffa2f50a3e5ee90e10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-8900000000-eccaa3c6c71a7aab8dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-fd3f3045e508262e68beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3390000000-ec3717ed507fec531202View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9520000000-06ed24b7ccb74ccd705bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9000000000-40bdb35b370bc3317a55View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Kidney
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.35-0.75 uMAdult (>18 years old)Both
Normal
details
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
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal 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
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD 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. doi: 10.1053/j.ajkd.2007.09.020. [PubMed: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. [PubMed: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
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:14741043 ]