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

• ChemBase ID: 11
• Molecular Formular: C6H14N4O2
• Molecular Mass: 174.20096
• Monoisotopic Mass: 174.11167571
• SMILES: C(CCNC(=N)N)[C@@H](C(=O)O)N
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)O)N
• 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
• InChIKey: ODKSFYDXXFIFQN-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: L-arginine
• Brand Name: R-Gene 10 (Pharmacia Corp.); Levargin; Minophagen A; Argivene; Argamine; Detoxargin
• Synonyms: Arginine; (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid; 2-Amino-5-guanidinovaleric acid; L-(+)-Arginine; L-a-Amino-d-guanidinovaleric acid; L-Arg; L-Arginine; 2-Amino-5-Guanidnovaleric Acid; (S)-2-Amino-5-guanidinopentanoic acid; Arg; R; L-ARGININE FREE BASE; 2-Amino-5-guanidinopentanoic acid; Arginine; L-Arginine; L-2-Amino-5-guanidinopentanoic acid; H-Arg-OH; (S)-2-氨基-5-胍基戊酸; L-精氨酸

Database IDs

• CAS Number: 74-79-3; 7200-25-1
• EC Number: 200-811-1; 230-571-3
• MDL Number: MFCD00002635
• Beilstein Number: 1725411, 1725412 R, 1725413 S; 1725413
• Merck Index: 14780
• PubChem SID: 24890870; 24891316; 46507180; 160963474; 24278014; 24846956; 24901894
• PubChem CID: 232; 6322
• CHEBI ID: 29016
• ATC CODE: B05XB01
• CHEMBL: 212301
• Chemspider ID: 227
• DrugBank ID: DB00125
• FEMA ID: 3819
• Gmelin ID: 364938 R
• IUPHAR ligand ID: 721
• KEGG ID: C02385
• MeSH Name: Arginine
• Unique Ingredient Identifier: 94ZLA3W45F
• Wikipedia Title: Arginine
• Flavis Number: 17.003

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4118392
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -6.1142516
• LogD (pH = 7.4): -5.121845
• Log P: -3.1615653
• Molar Refractivity: 53.9231 cm^3
• Polarizability: 16.904032 Å^3
• Polar Surface Area: 125.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.49
• LOG S: -1.88
• Solubility (Water): 2.28e+00 g/l

PROPERTIES

Physical Property

• Solubility: 182 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 87.1 g L^-1 (at 20 °C) in water; H2O: soluble100 mg/mL; H2O: soluble50 mg/mL
• Apperance: powder; White crystals; white powder
• Melting Point: 222 °C (dec.)(lit.); 222-225°C; 226°C dec.; 259.85°C (533K)
• Partition Coefficient: -1.652
• Optical Rotation: [α]20/D +27.0±0.5°, c = 5% in 5 M HCl; [α]20/D +27°, c = 8 in 6 M HCl; [α]24/D +26.1°, c = 1.6 in 6 M HCl; +26 (c=1.6 in 6N HCl)
• Absorption Wavelength: λ: 280 nm Amax: ≤0.1
• Hydrophobicity(logP): -3.6
• pKa: 2.488
• pKb: 11.509
• Odor: Odourless
• Heat Capacity: 232.8 J K^-1 mol^-1 (at 23.7 °C)
• Std enthalpy of combustion: -3.7396–-3.7370 MJ mol^-1
• Std enthalpy of formation: -624.9–-622.3 kJ mol^-1
• Std molar entropy: 250.6 J K^-1 mol^-1
• pH: 10.5-12.0 (25 °C, 0.5 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Air Sensitive; IRRITANT
• RTECS: CF1934200; CF1934200 S
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36; R:36/37/38; r36
• Safety Statements: 26; S:20-25-26-37/39; s26
• TSCA Listed: false; 是
• GHS Pictograms: GHS exclamation mark; GHS07
• GHS Signal Word: WARNING
• GHS Hazard statements: 319; H319
• GHS Precautionary statements: 305+351+338; P280-P264-P305+P351+P338-P337+P313
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 20-25°C
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

Pharmacology Properties

• Gene Information: human ... NOS1(4842), NOS2(4843); human ... NOS1(4842), NOS2(4843)rat ... Ppm1a(24666)
• Allergens: no known allergens

Product Information

• Purity: >98.5%; ≥98%; ≥98% (TLC); ≥98.0%; ≥98.5%; ≥99.5% (NT); 98%; 98.5-101.0%; 98+%; 99%
• Grade: EP; NI; PharmaGrade; reagent grade; SAJ special grade; USP
• Suitability: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.05% (as SO4)
• Impurities: ≤0.3% foreign amino acids; endotoxin, tested
• Cation Traces: Zn: ≤5 mg/kg
• Antion Traces: sulfate (SO42-): ≤100 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.1% loss on drying, 20 °C (HV)
• Quality Level: GMP-COMPENDIA
• λ: 0.5 M in H2O
• Linear Formula: H2NC(=NH)NH(CH2)3CH(NH2)CO2H

DETAILS

MP Biomedicals - 02100736

Crystalline
Purity: 99%

MP Biomedicals - 02194626

Cell Culture Reagent
Free Base
Purity: 99%

MP Biomedicals - 05201612

MP Biomedicals Rare Chemical collection

DrugBank - DB00125

• Drug Groups: approved; nutraceutical
• Description: An essential amino acid that is physiologically active in the L-form. [PubChem]
• Indication: Used for nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: Studies have shown that is has improved immune responses to bacteria, viruses and tumor cells; promotes wound healing and regeneration of the liver; causes the release of growth hormones; considered crucial for optimal muscle growth and tissue repair.
• Toxicity: Oral supplementation with L-arginine at doses up to 15 grams daily are generally well tolerated. The most common adverse reactions of higher doses from 15 to 30 grams daily are nausea, abdominal cramps and diarrhea. Some may experience these symptoms at lower doses.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Absorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.
• References: Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. [Pubmed] ; Schulman SP, Becker LC, Kass DA, Champion HC, Terrin ML, Forman S, Ernst KV, Kelemen MD, Townsend SN, Capriotti A, Hare JM, Gerstenblith G: L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial. JAMA. 2006 Jan 4;295(1):58-64. [Pubmed] ; Alba-Roth J, Muller OA, Schopohl J, von Werder K: Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion. J Clin Endocrinol Metab. 1988 Dec;67(6):1186-9. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - 11009

Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Other Notes
Exhibits stabilizing effects on plant protoplasts1; pH drift correction in IEF of proteins2; Growth requirement of various microorganisms3.

Sigma Aldrich - A8094

Biochem/physiol Actions
一氧化氮合成酶的底物，可转化为瓜氨酸和一氧化氮 (NO)。通过与一氧化氮相关的机理诱导胰岛素释放。
包装
10 mg in autosmp vl

Sigma Aldrich - A4474

Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Packaging
Manufactured and Packaged under cGMP.

Sigma Aldrich - A92406

Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.

Sigma Aldrich - W381918

Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.
Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10 kg in poly drum

Sigma Aldrich - A5006

Biochem/physiol Actions
一氧化氮合成酶的底物，可转化为瓜氨酸和一氧化氮 (NO)。通过与一氧化氮相关的机理诱导胰岛素释放。
包装
1 kg in poly bottle
100, 500 g in poly bottle

Sigma Aldrich - 01-6430

Biochem/physiol Actions
Substrate of nitric oxide synthase, which is converted to citrulline and nitric oxide (NO). Induces insulin release by a nitric oxide-dependent mechanism.

REFERENCES

• Morris SM Jr: Enzymes of arginine metabolism. J Nutr. 2004 Oct;134(10 Suppl):2743S-2747S; discussion 2765S-2767S. Pubmed
• Schulman SP, Becker LC, Kass DA, Champion HC, Terrin ML, Forman S, Ernst KV, Kelemen MD, Townsend SN, Capriotti A, Hare JM, Gerstenblith G: L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial. JAMA. 2006 Jan 4;295(1):58-64. Pubmed
• Alba-Roth J, Muller OA, Schopohl J, von Werder K: Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion. J Clin Endocrinol Metab. 1988 Dec;67(6):1186-9. Pubmed