Livestock Metabolome Database: Showing metabocard for Symmetric dimethylarginine (LMDB00425)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:34 UTC

Update Date

2016-08-06 20:10:08 UTC

Lmdb

LMDB00425

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Symmetric dimethylarginine

Description

Symmetric dimethylarginine, also known as N(g1),N(g2)-dimethylarginine or SDMA, 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. Symmetric dimethylarginine has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and pulses. This could make symmetric dimethylarginine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Symmetric dimethylarginine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoic acid	ChEBI
(S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoic acid	ChEBI
Guanidino-N(1),N(2)-dimethylarginine	ChEBI
N(g1),N(g2)-Dimethylarginine	ChEBI
N,N'-dimethylarginine	ChEBI
N(3),N(4)-Dimethyl-L-arginine	ChEBI
N(3),N(4)-Dimethylarginine	ChEBI
N5-((Methylamino)(methylimino)methyl)-L-ornithine	ChEBI
N(5)-(N,N'-dimethylamidino)-L-ornithine	ChEBI
N(5)-(N,N'-dimethylcarbamimidoyl)-L-ornithine	ChEBI
N(5)-[Bis(methylamino)methylene]-L-ornithine	ChEBI
N(g),N'(g)-dimethyl-L-arginine	ChEBI
N(g),N'(g)-dimethylarginine	ChEBI
SDMA	ChEBI
(2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoate	Generator
(S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoate	Generator
N5-(N,N'-dimethylamidino)-L-ornithine	HMDB
N5-[Bis(methylamino)methylene]-L-ornithine	HMDB
NG,N'G-dimethyl-L-arginine	HMDB, MeSH
NG,N'G-dimethylarginine	HMDB
NG,NG'-dimethylarginine	HMDB
Omega-N(g),n'(g)-dimethylarginine	MeSH, HMDB
SDMA arginine	MeSH, HMDB

Chemical Formula

C₈H₁₈N₄O₂

Average Molecular Weight

202.2541

Monoisotopic Molecular Weight

202.14297584

IUPAC Name

(2S)-2-amino-5-[(E)-N',N''-dimethylcarbamimidamido]pentanoic acid

Traditional Name

N3, N4-dimethylarginine

CAS Registry Number

30344-00-4

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 Key

HVPFXCBJHIIJGS-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
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 Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:25682 )
non-proteinogenic L-alpha-amino acid (CHEBI:25682 )
L-arginine derivative (CHEBI:25682 )
dimethylarginine (CHEBI:25682 )

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	-2.9	ALOGPS
logP	-2.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	12.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.18 m³·mol⁻¹	ChemAxon
Polarizability	22.22 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kfx-9600000000-f6c986d30ea287579a78	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fkc-9720000000-0f297fd1183458956770	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, Positive	splash10-00di-9600000000-a9cb6507d9fe3ffb39aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-053r-3910000000-1a8526e47c9af75d4cc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-9400000000-777d41b210dd091439b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pbi-1930000000-98ffa2f50a3e5ee90e10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-8900000000-eccaa3c6c71a7aab8dd3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-fd3f3045e508262e68be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3390000000-ec3717ed507fec531202	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9520000000-06ed24b7ccb74ccd705b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9000000000-40bdb35b370bc3317a55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2190000000-1ff257e4be06b9702e65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9100000000-b9dfe8a8d6f891dcecbf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-926c9fc48c09f4030499	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ue9-1590000000-567e7d20ebbf052f8d39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900000000-84e3189b175eab73e2c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-c8ec00d7abbc06aa7e4c	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
1D NMR	1H 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	Bovine	20647382	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	0.66 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.67 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.86 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.92 uM	Not Available	Porcine	Barbara U. Metzle...	details

External Links

DrugBank ID

DB02302

HMDB ID

HMDB0003334

FooDB ID

FDB000509

Phenol Explorer ID

Not Available

KNApSAcK ID

C00052415

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

6891

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

147942

ChEBI ID

25682

PubChem Compound ID

169148

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Symmetric dimethylarginine (LMDB00425)

Structure for LMDB00425 (Symmetric dimethylarginine)