AFCDB: Arginine (FDB002257)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:18 UTC

Update date

2024-11-29 22:26:49 UTC

Primary ID

FDB002257

Secondary Accession Numbers

FDB030954

Chemical Information

FooDB Name

Arginine

Description

Arginine or l-arginine, abbreviated Arg or R, is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Pre-term infants are unable to effectively synthesize arginine, making it nutritionally essential for them. Adults, however, synthesize arginine from glutamate via citrulline. Arginine is a basic amino acid as its side chain contains a positively charged guanidinium group, which is highly polar, at the end of a hydrophobic aliphatic hydrocarbon chain. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is a precursor of nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of the hormones, growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. While many studies suggested that plant based protein-rich foods like soy protein, which contain less arginine, reduced cardiovascular risk compared to arginine rich foods like animal proteins, other studies have found little or null effects (PMID: 20042191).

CAS Number

74-79-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.28 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-3.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	12.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	125.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.92 m³·mol⁻¹	ChemAxon
Polarizability	17.8 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

C6H14N4O2

IUPAC name

(2S)-2-amino-5-carbamimidamidopentanoic acid

InChI Identifier

InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1

InChI Key

ODKSFYDXXFIFQN-BYPYZUCNSA-N

Isomeric SMILES

N[C@@H](CCCNC(N)=N)C(O)=O

Average Molecular Weight

174.201

Monoisotopic Molecular Weight

174.111675712

Classification

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

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
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16467 )
L-alpha-amino acid (CHEBI:16467 )
arginine (CHEBI:16467 )
glutamine family amino acid (CHEBI:16467 )
Common amino acids (C00062 )

Ontology

Heart failure

Cancer:

Leukemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Lysinuric protein intolerance

Role

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 41.37%; H 8.10%; N 32.16%; O 18.37%	DFC
Melting Point	Mp 244 dec. (anhyd. 105°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	182 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-4.20	HANSCH,C ET AL. (1995)
Experimental pKa	pKa3 12.48 (guanido)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D +48.1 (c, 1 in 5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Arginine, 3 TMS, GC-MS Spectrum	splash10-0a4i-1910000000-0191c1a63652c493660b	Spectrum
GC-MS	Arginine, 3 TMS, GC-MS Spectrum	splash10-00di-9810000000-eb6eb73302b678cf0a24	Spectrum
GC-MS	Arginine, 2 TMS, GC-MS Spectrum	splash10-00di-9700000000-e47b41cff0e873f53932	Spectrum
GC-MS	Arginine, 3 TMS, GC-MS Spectrum	splash10-0a4i-1920000000-8ae5af11398835d26bed	Spectrum
GC-MS	Arginine, non-derivatized, GC-MS Spectrum	splash10-0a4i-1910000000-0191c1a63652c493660b	Spectrum
GC-MS	Arginine, non-derivatized, GC-MS Spectrum	splash10-00di-9810000000-eb6eb73302b678cf0a24	Spectrum
GC-MS	Arginine, non-derivatized, GC-MS Spectrum	splash10-00di-9700000000-e47b41cff0e873f53932	Spectrum
GC-MS	Arginine, non-derivatized, GC-MS Spectrum	splash10-0a4i-1920000000-8ae5af11398835d26bed	Spectrum
GC-MS	Arginine, non-derivatized, GC-MS Spectrum	splash10-0udi-0900000000-afc3ca93f8fbf54ec9f4	Spectrum
Predicted GC-MS	Arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9100000000-60db59de76b9a9b5bfc8	Spectrum
Predicted GC-MS	Arginine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-8900000000-f47c4f9480612fdbc962	Spectrum
Predicted GC-MS	Arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Arginine, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0fk9-0946231100-3d57d2304dcb33feab3f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-000i-0900000000-5b6dd6fb263ea09289fc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-dfe35b3438d19320d8cb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-f666ab7e5354bce67a2e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03kd-0977452210-046c4b70bd0ec351c41d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-014i-9000000000-2f51e43e530976d63633	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-b9ebb7ebccee1a313888	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-5379b6fb6ea2313101f9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-835751d54af24bd337e7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-2d2b5fd7617ccb227bb1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-dfe35b3438d19320d8cb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0900000000-f666ab7e5354bce67a2e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-b9ebb7ebccee1a313888	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0900000000-5379b6fb6ea2313101f9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-835751d54af24bd337e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-2d2b5fd7617ccb227bb1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-8e090b4f0a569ec011b3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-647e6324d4041e9d5cc1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d866a7f7b1bf575941ee	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-c3a3ef3d4f3627781019	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-3900000000-8c82418f7b35a97fb9b3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-19b62da79866318c52dd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-64b046d21bdcbb8d5923	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-e07b937b6867d1f62293	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-87ab853583aab2973cfb	2012-08-31	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16467

Phenol-Explorer ID

Not Available

DrugBank ID

DB00125

HMDB ID

HMDB00517

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1068131

SuperScent ID

Not Available

Wikipedia ID

Arginine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti encephalopathic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hepatitic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti hypertensive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti impotence	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti infertility	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
aphrodisiac			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
hypoammonemic			DUKE
nitric-oxide-genic			DUKE
pituitary stimulant			DUKE
spermigenic			DUKE
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Glycine amidinotransferase, mitochondrial	GATM	P50440
Arginine--tRNA ligase, cytoplasmic	RARS	P54136
Argininosuccinate synthase	ASS1	P00966
Argininosuccinate lyase	ASL	P04424
Arginine decarboxylase	ADC	Q96A70
High affinity cationic amino acid transporter 1	SLC7A1	P30825
Probable arginine--tRNA ligase, mitochondrial	RARS2	Q5T160
NOS1 mutant	NOS1	B3VK56
[Protein ADP-ribosylarginine] hydrolase	ADPRH	P54922

Pathways

Name	SMPDB Link	KEGG Link
Arginine and Proline Metabolism	SMP00020	map00330
Glycine and Serine Metabolism	SMP00004	map00260
Transcription/Translation	SMP00019	Not Available
Urea Cycle	SMP00059	map00330
Metabolism and Physiological Effects of Putrescine	SMP0123276	Not Available
Metabolism and Physiological Effects of Creatinine	SMP0123283	Not Available
Metabolism and Phsyiological Effects of Asymmetric dimethylarginine (ADMA)	SMP0124747	Not Available
Metabolism and Physiological Effects of Symmetric dimethylarginine (SDMA)	SMP0124764	Not Available
Metabolsim and Physiological Effects of Argininic acid	SMP0125504	Not Available
Metabolism and Physiological Effects of N-alpha-Acetyl-L-arginine	SMP0125530	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
faint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Arginine (FDB002257)

Structure for FDB002257 (Arginine)