Showing Compound NG,N'G-Dimethyl-L-arginine (FDB000509)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:36 UTC

Update date

2019-11-26 02:54:55 UTC

Primary ID

FDB000509

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

NG,N'G-Dimethyl-L-arginine

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.

CAS Number

30344-00-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
(2S)-2-amino-5-(N',n''-dimethylcarbamimidamido)pentanoate	Generator
(2S)-2-amino-5-(N',n''-dimethylcarbamimidamido)pentanoic acid	ChEBI
(S)-2-amino-5-(N',n''-dimethylguanidino)pentanoate	Generator
(S)-2-amino-5-(N',N''-dimethylguanidino)pentanoic acid	biospider
L-Ornithine, N5-((methylamino)(methylimino)methyl)-	biospider
N(G1),N(G2)-Dimethylarginine	biospider
N5-((methylamino)(methylimino)methyl)-L-Ornithine	biospider
N5-(N,N'-dimethylamidino)-L-Ornithine	biospider
N5-[bis(methylamino)methylene]-L-Ornithine	biospider
NG,N'G-Dimethyl-L-arginine	biospider
NG,n'g-dimethylarginine	HMDB
NG,N'G-Dimethylarginine; L-form	db_source
NG,ng'-dimethylarginine	HMDB
Symmetric dimethylarginine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	1.56 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H18N4O2

IUPAC name

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

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

Isomeric SMILES

CN\C(NCCC[C@H](N)C(O)=O)=N/C

Average Molecular Weight

202.2541

Monoisotopic Molecular Weight

202.14297584

Classification

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

Dermal

Enteral:

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Biofluid and excreta:

Organ and components:

Kidney

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 47.51%; H 8.97%; N 27.70%; O 15.82%	DFC
Melting Point	Mp 237-239° (diflavianate)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	NG,N'G-Dimethyl-L-arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kfx-9600000000-f6c986d30ea287579a78	Spectrum
Predicted GC-MS	NG,N'G-Dimethyl-L-arginine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fkc-9720000000-0f297fd1183458956770	Spectrum
Predicted GC-MS	NG,N'G-Dimethyl-L-arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	NG,N'G-Dimethyl-L-arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9600000000-a9cb6507d9fe3ffb39aa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-053r-3910000000-1a8526e47c9af75d4cc9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-9400000000-777d41b210dd091439b4	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pbi-1930000000-98ffa2f50a3e5ee90e10	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-8900000000-eccaa3c6c71a7aab8dd3	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-fd3f3045e508262e68be	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3390000000-ec3717ed507fec531202	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9520000000-06ed24b7ccb74ccd705b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9000000000-40bdb35b370bc3317a55	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2190000000-1ff257e4be06b9702e65	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9100000000-b9dfe8a8d6f891dcecbf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-926c9fc48c09f4030499	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ue9-1590000000-567e7d20ebbf052f8d39	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900000000-84e3189b175eab73e2c5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-c8ec00d7abbc06aa7e4c	2021-09-24	View Spectrum