Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:18 UTC |
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Update date | 2020-09-17 15:38:36 UTC |
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Primary ID | FDB002257 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Arginine |
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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). |
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CAS Number | 74-79-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(2S)-2-Amino-5-(carbamimidamido)pentanoic acid | ChEBI | (2S)-2-Amino-5-guanidinopentanoic acid | ChEBI | (S)-2-Amino-5-guanidinopentanoic acid | ChEBI | (S)-2-Amino-5-guanidinovaleric acid | ChEBI | Arg | ChEBI | Arginine | ChEBI | L-(+)-Arginine | ChEBI | L-Arg | ChEBI | L-Arginin | ChEBI | R | ChEBI | (2S)-2-Amino-5-(carbamimidamido)pentanoate | Generator | (2S)-2-Amino-5-guanidinopentanoate | Generator | (S)-2-Amino-5-guanidinopentanoate | Generator | (S)-2-Amino-5-guanidinovalerate | Generator | (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoate | HMDB | (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acid | HMDB | (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoate | HMDB | (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid | HMDB | 2-Amino-5-guanidinovalerate | HMDB | 2-Amino-5-guanidinovaleric acid | HMDB | 5-[(Aminoiminomethyl)amino]-L-norvaline | HMDB | L-a-Amino-D-guanidinovalerate | HMDB | L-a-Amino-D-guanidinovaleric acid | HMDB | L-alpha-Amino-delta-guanidinovalerate | HMDB | L-alpha-Amino-delta-guanidinovaleric acid | HMDB | N5-(Aminoiminomethyl)-L-ornithine | HMDB | DL-Arginine acetate, monohydrate | HMDB | L-Isomer arginine | HMDB | Monohydrate DL-arginine acetate | HMDB | L Arginine | HMDB | Arginine, L isomer | HMDB | Arginine, L-isomer | HMDB | Hydrochloride, arginine | HMDB | Arginine hydrochloride | HMDB | DL Arginine acetate, monohydrate | HMDB | (2S)-2-amino-5-(Carbamimidamido)pentanoate | Generator | (2S)-2-Amino-5-(diaminomethylideneamino)pentanoic acid | biospider | (2S)-2-amino-5-Guanidinopentanoate | Generator | (S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoate | HMDB | (S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoic acid | HMDB | (S)-2-amino-5-Guanidinopentanoate | Generator | (S)-2-amino-5-Guanidinovalerate | Generator | 2-amino-5-Guanidinovalerate | HMDB | 2-amino-5-Guanidinovaleric acid | HMDB | 5-[(Aminoiminomethyl)amino]-L-Norvaline | biospider | Arginine, INN, USAN; L-form | db_source | FEMA 3819 | db_source | L-a-Amino-d-guanidinovalerate | biospider | L-a-Amino-d-guanidinovaleric acid | biospider | L-Arginine | ChEBI | L-Arginine (9CI) | biospider | Pentanoic acid, 2-amino-5-((aminoiminomethyl)amino)-, (S)- | biospider | S-(+)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid | biospider | S-Arginine | manual |
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Predicted Properties | |
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Chemical Formula | C6H14N4O2 |
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IUPAC name | (2S)-2-amino-5-carbamimidamidopentanoic acid |
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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 |
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InChI Key | ODKSFYDXXFIFQN-BYPYZUCNSA-N |
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Isomeric SMILES | N[C@@H](CCCNC(N)=N)C(O)=O |
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Average Molecular Weight | 174.201 |
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Monoisotopic Molecular Weight | 174.111675712 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 41.37%; H 8.10%; N 32.16%; O 18.37% | DFC |
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Melting Point | Mp 244 dec. (anhyd. 105°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 182 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | -4.20 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa3 12.48 (guanido) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]25D +48.1 (c, 1 in 5M HCl) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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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 |
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MS/MS | Type | Description | Splash Key | View |
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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 |
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NMR | Type | Description | | View |
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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 |
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External Links |
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ChemSpider ID | 6082 |
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ChEMBL ID | CHEMBL1485 |
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KEGG Compound ID | C00062 |
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Pubchem Compound ID | 6322 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16467 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00125 |
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HMDB ID | HMDB00517 |
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CRC / DFC (Dictionary of Food Compounds) ID | CHQ98-B:CHQ90-T |
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EAFUS ID | 248 |
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Dr. Duke ID | L-ARGININE|ARGININE |
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BIGG ID | 33707 |
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KNApSAcK ID | C00001340 |
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HET ID | 1FOL |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1068131 |
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SuperScent ID | Not Available |
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Wikipedia ID | Arginine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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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 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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faint |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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).
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