Livestock Metabolome Database: Showing metabocard for Asymmetric dimethylarginine (LMDB00344)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:45 UTC

Update Date

2021-04-30 20:57:41 UTC

Lmdb

LMDB00344

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Asymmetric dimethylarginine

Description

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 animal 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
ADMA	ChEBI
Guanidino-N,N-dimethylarginine	ChEBI
N,N-Dimethylarginine	ChEBI
N(5)-((Dimethylamino)iminomethyl)-L-ornithine	ChEBI
NG,NG-Dimethyl-L-arginine	ChEBI
N(g),N(g)-Dimethylarginine	ChEBI
N(g)-Dimethylarginine	ChEBI
N(g1),N(g1)-Dimethylarginine	ChEBI
Nomega,nomega-dimethyl-L-arginine	Kegg
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoate	HMDB
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid	HMDB
Dimethyl-L-arginine	HMDB
N(Omega),N(omega)-dimethyl-L-arginine	HMDB
NG,NG-Dimethylarginine	HMDB
NG-Dimethylarginine	HMDB
Nomega,nomega'-dimethyl-L-arginine	HMDB
Asymmetric dimethylarginine	ChEBI

Chemical Formula

C₈H₁₈N₄O₂

Average Molecular Weight

202.2541

Monoisotopic Molecular Weight

202.14297584

IUPAC Name

(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid

Traditional Name

asymmetric dimethylarginine

CAS Registry Number

30315-93-6

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 Key

YDGMGEXADBMOMJ-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.

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:17929 )
non-proteinogenic L-alpha-amino acid (CHEBI:17929 )
L-arginine derivative (CHEBI:17929 )
dimethylarginine (CHEBI:17929 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.1	ALOGPS
logP	-2.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	12.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.7 m³·mol⁻¹	ChemAxon
Polarizability	22.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9300000000-4fc2a444d078a1eb4d85	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9520000000-928759e33b3f9821da4a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9100000000-2849c1945541be90da8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9200000000-f7af59f4a85b35ee2239	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9310000000-901ceea58124eb646d2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pbi-1930000000-6a12bc30dbe08d316d09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-8900000000-47e0a5a868dce918c9b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-d674ec18daa47f080be4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3390000000-2b624585e91010265a57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-9420000000-b8fe15104f41182b9d9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9100000000-120212bd5d151152c8ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-9370000000-4bea91f4d0256a94739f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-2900000000-8fc254a7c96b0565c1ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-428e5ae3fbdfa34b338c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-2690000000-5766392f870c77d53359	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9200000000-a7b438425f1f49a1a48b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-e6f7e053fa2072aa45ff	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Serum	Detected and Quantified	3.4363 +/- 0.7212 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.0728 +/- 0.2533 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5813 +/- 1.1628 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.1996 +/- 0.5792 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.11 +/- 1.44 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	3.3916 +/- 0.8669 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.2558 +/- 0.6288 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.2 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	1.3 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	1.4 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	1.4 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	3.3335 +/- 0.7206 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.0738 +/- 0.2923 uM	Normal	Ovine	Goldansaz et al.,...	details