L-ARGININE
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | L-ARGININE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 74-79-3 |
| Regnum |
172.320 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6322 |
| IUPAC Name | (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid |
| InChI | 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 |
| Canonical SMILES | C(CC(C(=O)O)N)CN=C(N)N |
| Molecular Formula | C6H14N4O2 |
| Wikipedia | arginine hydrochloride |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 174.204 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 176.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B j s A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A Q C A A A C C j B g A Q B C A J A A g A o A A C Q L A A A A A E A A A A A A I G A A A A C A B I A g A A A Q A A E E A A A A A C Y E Q A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 128.0 |
| Monoisotopic Mass | 174.112 |
| Exact Mass | 174.112 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6926 |
| Human Intestinal Absorption | HIA+ | 0.7537 |
| Caco-2 Permeability | Caco2- | 0.7315 |
| P-glycoprotein Substrate | Non-substrate | 0.5352 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9846 |
| Non-inhibitor | 0.9156 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7389 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6201 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7939 |
| CYP450 2D6 Substrate | Non-substrate | 0.6806 |
| CYP450 3A4 Substrate | Non-substrate | 0.7967 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8006 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9251 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9270 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8813 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9954 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9590 |
| Non-inhibitor | 0.9709 | |
| AMES Toxicity | AMES toxic | 0.6882 |
| Carcinogens | Non-carcinogens | 0.9304 |
| Fish Toxicity | Low FHMT | 0.8565 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.7700 |
| Honey Bee Toxicity | Low HBT | 0.7135 |
| Biodegradation | Ready biodegradable | 0.7386 |
| Acute Oral Toxicity | IV | 0.6176 |
| Carcinogenicity (Three-class) | Non-required | 0.6495 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.4289 | LogS |
| Caco-2 Permeability | -0.0394 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5310 | LD50, mol/kg |
| Fish Toxicity | 2.6933 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3374 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Absorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism. |
|---|---|
| Mechanism of Toxicity | Many of supplemental L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide or NO. NO is produced by all tissues of the body and plays very important roles in the cardiovascular system, immune system and nervous system. NO is formed from L-arginine via the enzyme nitric oxide synthase or synthetase (NOS), and the effects of NO are mainly mediated by 3,'5' -cyclic guanylate or cyclic GMP. NO activates the enzyme guanylate cyclase, which catalyzes the synthesis of cyclic GMP from guanosine triphosphate or GTP. Cyclic GMP is converted to guanylic acid via the enzyme cyclic GMP phosphodiesterase. NOS is a heme-containing enzyme with some sequences similar to cytochrome P-450 reductase. Several isoforms of NOS exist, two of which are constitutive and one of which is inducible by immunological stimuli. The constitutive NOS found in the vascular endothelium is designated eNOS and that present in the brain, spinal cord and peripheral nervous system is designated nNOS. The form of NOS induced by immunological or inflammatory stimuli is known as iNOS. iNOS may be expressed constitutively in select tissues such as lung epithelium. All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen as cosubstrates, as well as the cofactors FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), tetrahydrobiopterin and heme. Interestingly, ascorbic acid appears to enhance NOS activity by increasing intracellular tetrahydrobiopterin. eNOS and nNOS synthesize NO in response to an increased concentration of calcium ions or in some cases in response to calcium-independent stimuli, such as shear stress. In vitro studies of NOS indicate that the Km of the enzyme for L-arginine is in the micromolar range. The concentration of L-arginine in endothelial cells, as well as in other cells, and in plasma is in the millimolar range. What this means is that, under physiological conditions, NOS is saturated with its L-arginine substrate. In other words, L-arginine would not be expected to be rate-limiting for the enzyme, and it would not appear that supraphysiological levels of L-arginine which could occur with oral supplementation of the amino acid^would make any difference with regard to NO production. The reaction would appear to have reached its maximum level. However, in vivo studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, supplemental L-arginine could enhance endothelial-dependent vasodilation and NO production. |
| Metabolism | Some metabolism of L-arginine takes place in the enterocytes. L-arginine not metabolized in the enterocytes enters the portal circulation from whence it is transported to the liver, where again some portion of the amino acid is metabolized. |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids |
| Direct Parent | L-alpha-amino acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound 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. |
From ClassyFire
Targets
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor.
- Gene Name:
- SLC7A1
- Uniprot ID:
- P30825
- Molecular Weight:
- 67637.62 Da
References
- Cerec V, Piquet-Pellorce C, Aly HA, Touzalin AM, Jegou B, Bauche F: Multiple pathways for cationic amino acid transport in rat seminiferous tubule cells. Biol Reprod. 2007 Feb;76(2):241-9. Epub 2006 Oct 25. [17065601 ]
- General Function:
- Tetrahydrobiopterin binding
- Specific Function:
- Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
- Gene Name:
- NOS3
- Uniprot ID:
- P29474
- Molecular Weight:
- 133287.62 Da
References
- Haruna Y, Morita Y, Komai N, Yada T, Sakuta T, Tomita N, Fox DA, Kashihara N: Endothelial dysfunction in rat adjuvant-induced arthritis: vascular superoxide production by NAD(P)H oxidase and uncoupled endothelial nitric oxide synthase. Arthritis Rheum. 2006 Jun;54(6):1847-55. [16729278 ]
- General Function:
- Putrescine transmembrane transporter activity
- Specific Function:
- Antizyme inhibitor protein that positively regulates ornithine decarboxylase (ODC) activity and polyamine uptake by counteracting the negative effect of antizymes OAZ1, OAZ2 and OAZ3 on ODC1 activity (PubMed:17900240). Inhibits antizyme-dependent ODC1 degradation by binding to antizymes. Releases ODC1 from its inactive complex with antizymes, leading to formation of the catalytically active ODC1. Participates in the morphological integrity of the trans-Golgi network (TGN) and functions as a regulator of intracellular secretory vesicle trafficking (PubMed:20188728).
- Gene Name:
- AZIN2
- Uniprot ID:
- Q96A70
- Molecular Weight:
- 49979.185 Da
References
- Wu N, Su RB, Li J: Agmatine and imidazoline receptors: their role in opioid analgesia, tolerance and dependence. Cell Mol Neurobiol. 2008 Aug;28(5):629-41. Epub 2007 Jul 25. [17653850 ]
- General Function:
- Toxic substance binding
- Specific Function:
- Is indirectly involved in the control of blood pressure.
- Gene Name:
- ASS1
- Uniprot ID:
- P00966
- Molecular Weight:
- 46530.055 Da
References
- Szlosarek PW, Grimshaw MJ, Wilbanks GD, Hagemann T, Wilson JL, Burke F, Stamp G, Balkwill FR: Aberrant regulation of argininosuccinate synthetase by TNF-alpha in human epithelial ovarian cancer. Int J Cancer. 2007 Jul 1;121(1):6-11. [17354225 ]
- General Function:
- Metal ion binding
- Specific Function:
- May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to NO synthase. Since NO synthase is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase II plays a role in both male and female sexual arousal. It is therefore a potential target for the treatment of male and female sexual arousal disorders.
- Gene Name:
- ARG2
- Uniprot ID:
- P78540
- Molecular Weight:
- 38577.515 Da
References
- Hood HM, Spevak CC, Sachs MS: Evolutionary changes in the fungal carbamoyl-phosphate synthetase small subunit gene and its associated upstream open reading frame. Fungal Genet Biol. 2007 Feb;44(2):93-104. Epub 2006 Sep 18. [16979358 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
- Gene Name:
- SLC7A3
- Uniprot ID:
- Q8WY07
- Molecular Weight:
- 67168.31 Da
References
- Huang Y, Kang BN, Tian J, Liu Y, Luo HR, Hester L, Snyder SH: The cationic amino acid transporters CAT1 and CAT3 mediate NMDA receptor activation-dependent changes in elaboration of neuronal processes via the mammalian target of rapamycin mTOR pathway. J Neurosci. 2007 Jan 17;27(3):449-58. [17234578 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Involved in the transport of the cationic amino acids (arginine, lysine and ornithine).
- Gene Name:
- SLC7A4
- Uniprot ID:
- O43246
- Molecular Weight:
- 68267.17 Da
References
- Rotmann A, Simon A, Martine U, Habermeier A, Closs EI: Activation of classical protein kinase C decreases transport via systems y+ and y+L. Am J Physiol Cell Physiol. 2007 Jun;292(6):C2259-68. Epub 2007 Feb 28. [17329401 ]
- General Function:
- Tetrahydrobiopterin binding
- Specific Function:
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM.
- Gene Name:
- NOS2
- Uniprot ID:
- P35228
- Molecular Weight:
- 131116.3 Da
References
- Martin NI, Woodward JJ, Winter MB, Marletta MA: 4,4-Difluorinated analogues of l-arginine and N(G)-hydroxy-l-arginine as mechanistic probes for nitric oxide synthase. Bioorg Med Chem Lett. 2009 Mar 15;19(6):1758-62. doi: 10.1016/j.bmcl.2009.01.076. Epub 2009 Feb 18. [19230661 ]
From T3DB