NAV

N,N-dimethylarginine

Identification

Generic Name
N,N-dimethylarginine
DrugBank Accession Number
DB01686
Background

Asymmetric 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 which 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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 202.2541
Monoisotopic: 202.14297584
Chemical Formula
C8H18N4O2
Synonyms
  • ADMA
  • Asymmetric dimethylarginine
  • dimethyl-L-arginine
  • guanidino-N,N-dimethylarginine
  • L-NG,NG-dimethylarginine
  • N(5)-((Dimethylamino)iminomethyl)-L-ornithine
  • N(G)-Dimethylarginine
  • N(G),N(G)-Dimethylarginine
  • N(G1),N(G1)-Dimethylarginine
  • NG,NG-Dimethyl-L-arginine
External IDs
  • Lopac-D-4268
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide synthase, is formed by methylation of arginine residues in proteins and released after proteolysis. In this reaction, S-adenosylmethionine is methyldonor and S-adenosylhomocysteine the demethylated product. ADMA and homocysteine are thus biochemically linked. Both plasma homocysteine and ADMA concentrations are increased in patients with renal dysfunction, probably as a result of an impairment in their metabolic, but not urinary, clearance. Hyperhomocysteinemia has been associated with an increased risk of cardiovascular disease in end-stage renal disease, especially in patients without malnutrition and inflammation. Also, plasma ADMA levels have been associated with cardiovascular disease in renal failure patients. Both homocysteine and ADMA are thought to mediate their adverse vascular effects by impairing endothelial, nitric oxide-dependent function resulting in decreased vasodilatation, increased smooth muscle cell proliferation, platelet dysfunction and increased monocyte adhesion.

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, inducibleNot AvailableHumans
UNitric oxide synthase, endothelialNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Arginine and derivatives
Alternative Parents
L-alpha-amino acids / Fatty acids and conjugates / Guanidines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 3 more
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Arginine or derivatives / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Guanidine
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
guanidines, non-proteinogenic L-alpha-amino acid, L-arginine derivative, dimethylarginine (CHEBI:17929)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
63CV1GEK3Y
CAS number
30315-93-6
InChI Key
YDGMGEXADBMOMJ-LURJTMIESA-N
InChI
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
IUPAC Name
(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid
SMILES
N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O

References

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. [Article]
Human Metabolome Database
HMDB0001539
KEGG Compound
C03626
PubChem Compound
123831
PubChem Substance
46508091
ChemSpider
110375
BindingDB
92901
ChEBI
17929
ChEMBL
CHEMBL457530
ZINC
ZINC000001529718
PDBe Ligand
DA2
Wikipedia
Asymmetric_dimethylarginine
PDB Entries
2b2u / 2lto / 2v86 / 2vpg / 4a4g / 4a4h / 4m5a / 4mzf / 5tdb / 5vah …
show 1 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.77 mg/mLALOGPS
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 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity53.7 m3·mol-1Chemaxon
Polarizability22.19 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8076
Blood Brain Barrier-0.57
Caco-2 permeable-0.6688
P-glycoprotein substrateSubstrate0.6229
P-glycoprotein inhibitor INon-inhibitor0.9691
P-glycoprotein inhibitor IINon-inhibitor0.8965
Renal organic cation transporterNon-inhibitor0.7389
CYP450 2C9 substrateNon-substrate0.8266
CYP450 2D6 substrateNon-substrate0.7315
CYP450 3A4 substrateNon-substrate0.6171
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9242
CYP450 2C19 inhibitorNon-inhibitor0.93
CYP450 3A4 inhibitorNon-inhibitor0.8462
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9962
Ames testNon AMES toxic0.6415
CarcinogenicityNon-carcinogens0.8837
BiodegradationNot ready biodegradable0.7658
Rat acute toxicity2.0460 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.944
hERG inhibition (predictor II)Non-inhibitor0.9228
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00dl-9300000000-4fc2a444d078a1eb4d85
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f6w-1920000000-352e317361bed495b71b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-3390000000-a01c390ed5de6a5bc26d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fai-1940000000-baed7410399a2da42607
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9300000000-45adffd031a2c8223a41
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-2900000000-669fd470990cec078105
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-cb578786a34472ac9c88
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9200000000-fe0092618f2fc7814228
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-158.0482423
predicted
DarkChem Lite v0.1.0
[M-H]-158.1098423
predicted
DarkChem Lite v0.1.0
[M-H]-158.1197423
predicted
DarkChem Lite v0.1.0
[M-H]-158.1132423
predicted
DarkChem Lite v0.1.0
[M-H]-151.4026
predicted
DeepCCS 1.0 (2019)
[M+H]+159.3653423
predicted
DarkChem Lite v0.1.0
[M+H]+159.4086423
predicted
DarkChem Lite v0.1.0
[M+H]+159.3359423
predicted
DarkChem Lite v0.1.0
[M+H]+159.4593423
predicted
DarkChem Lite v0.1.0
[M+H]+153.7606
predicted
DeepCCS 1.0 (2019)
[M+Na]+158.6974423
predicted
DarkChem Lite v0.1.0
[M+Na]+158.8636423
predicted
DarkChem Lite v0.1.0
[M+Na]+158.3366423
predicted
DarkChem Lite v0.1.0
[M+Na]+158.6071423
predicted
DarkChem Lite v0.1.0
[M+Na]+160.18135
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nitric oxide synthase, inducible
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
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 ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 Da
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. [Article]
Details2. Nitric oxide synthase, endothelial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
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)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 Da
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51