Bovine Metabolome Database: Showing metabocard for Dimethyl-L-arginine (BMDB0001539)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:23 UTC

Update Date

2020-06-04 19:39:56 UTC

BMDB ID

BMDB0001539

Secondary Accession Numbers

BMDB01539

Metabolite Identification

Common Name

Dimethyl-L-arginine

Description

Asymmetric dimethylarginine, also known as N(g),N(g)-dimethylarginine or guanidino-N,N-dimethylarginine, 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. Asymmetric dimethylarginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Asymmetric dimethylarginine exists in all eukaryotes, ranging from yeast to humans. Asymmetric dimethylarginine is a potentially toxic compound.

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

Solid

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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9300000000-4fc2a444d078a1eb4d85	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9520000000-928759e33b3f9821da4a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9100000000-2849c1945541be90da8a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9200000000-f7af59f4a85b35ee2239	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9310000000-901ceea58124eb646d2d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pbi-1930000000-6a12bc30dbe08d316d09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-8900000000-47e0a5a868dce918c9b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-d674ec18daa47f080be4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3390000000-2b624585e91010265a57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-9420000000-b8fe15104f41182b9d9b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9100000000-120212bd5d151152c8ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-9370000000-4bea91f4d0256a94739f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-2900000000-8fc254a7c96b0565c1ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-428e5ae3fbdfa34b338c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-2690000000-5766392f870c77d53359	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9200000000-a7b438425f1f49a1a48b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-e6f7e053fa2072aa45ff	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Kidney
Liver
Longissimus Thoracis Muscle
Milk
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.1 +/- 0.2 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected and Quantified	1.3-2.1 uM	Not Specified	Not Specified	Normal	PMID: 10764670	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected and Quantified	1 +/- 1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.8 +/- 0.2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Milk	Detected and Quantified	0.08 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.09 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.1 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	0.10 +/- 0.01 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	4 +/- 3 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	0.33 +/- 0.14 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semimembranosus Muscle	Detected and Quantified	0.9 +/- 0.2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.8 +/- 0.2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001539

DrugBank ID

DB01686

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000508

KNApSAcK ID

Not Available

Chemspider ID

110375

KEGG Compound ID

C03626

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Asymmetric dimethylarginine

METLIN ID

6309

PubChem Compound

123831

PDB ID

Not Available

ChEBI ID

17929

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for Dimethyl-L-arginine (BMDB0001539)

Structure for BMDB0001539 (Dimethyl-L-arginine)