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

• ChemBase编号: 11
• 分子式: C6H14N4O2
• 平均质量: 174.20096
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-5-carbamimidamidopentanoic acid
• IUPAC传统名: L-arginine
• 商标名: R-Gene 10 (Pharmacia Corp.); Levargin; Minophagen A; Argivene; Argamine; Detoxargin
• 别名: (S)-2-氨基-5-胍基戊酸; L-精氨酸; 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

登记号

• CAS号: 74-79-3; 7200-25-1
• EC号: 200-811-1; 230-571-3
• MDL号: MFCD00002635
• Beilstein号: 1725411, 1725412 R, 1725413 S; 1725413
• 默克索引号: 14780
• PubChem SID: 46507180; 24890870; 24278014; 24846956; 24891316; 160963474; 24901894
• PubChem CID: 232; 6322
• CHEBI ID: 29016
• ATC码: B05XB01
• CHEMBL: 212301
• Chemspider ID: 227
• DrugBank ID: DB00125
• FEMA编号: 3819
• Gmelin ID: 364938 R
• IUPHAR配体索引: 721
• KEGG ID: C02385
• 医学主题词(MeSH): Arginine
• 美国药典/FDA物质标识码: 94ZLA3W45F
• 维基百科标题: Arginine
• Flavis Number: 17.003

理论计算性质

JChem

• Acid pKa: 2.4118392
• 质子受体: 6
• 质子供体: 5
• LogD (pH = 5.5): -6.1142516
• LogD (pH = 7.4): -5.121845
• Log P: -3.1615653
• 摩尔折射率: 53.9231 cm^3
• 极化性: 16.904032 Å^3
• 极化表面积: 125.22 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -3.49
• LOG S: -1.88
• 溶解度: 2.28e+00 g/l

分子性质

理化性质

• 溶解度: 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
• 外观: powder; White crystals; white powder
• 熔点: 222 °C (dec.)(lit.); 222-225°C; 226°C dec.; 259.85°C (533K)
• 分配系数: -1.652
• 比旋光度: [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)
• 紫外吸收波长: λ: 280 nm Amax: ≤0.1
• 疏水性(logP): -3.6
• pKa: 2.488
• pKb: 11.509
• 气味: Odourless
• 热容: 232.8 J K^-1 mol^-1 (at 23.7 °C)
• 标准摩尔燃烧焓 (ΔcH^o298): -3.7396–-3.7370 MJ mol^-1
• 标准摩尔生成焓 (ΔfH^o298): -624.9–-622.3 kJ mol^-1
• 标准摩尔熵 (S^o298): 250.6 J K^-1 mol^-1
• pH值: 10.5-12.0 (25 °C, 0.5 M in H2O)

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: Air Sensitive; IRRITANT
• RTECS编号: CF1934200; CF1934200 S
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 36; R:36/37/38; r36
• 安全公开号: 26; S:20-25-26-37/39; s26
• TSCA收录: false; 是
• GHS危险品标识: GHS exclamation mark; GHS07
• GHS警示词: WARNING
• GHS危险声明: 319; H319
• GHS警示性声明: 305+351+338; P280-P264-P305+P351+P338-P337+P313
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 20-25°C
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

药理学性质

• 相关基因信息: human ... NOS1(4842), NOS2(4843); human ... NOS1(4842), NOS2(4843)rat ... Ppm1a(24666)
• 过敏源: no known allergens

产品相关信息

• 纯度: >98.5%; ≥98%; ≥98% (TLC); ≥98.0%; ≥98.5%; ≥99.5% (NT); 98%; 98.5-101.0%; 98+%; 99%
• 级别: EP; NI; PharmaGrade; reagent grade; SAJ special grade; USP
• 适用性: meets EP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.05% (as SO4)
• 杂质: ≤0.3% foreign amino acids; endotoxin, tested
• 痕量阳离子: Zn: ≤5 mg/kg
• 痕量阴离子: sulfate (SO42-): ≤100 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.1% loss on drying, 20 °C (HV)
• 产品质量级别: GMP-COMPENDIA
• λ: 0.5 M in H2O
• 线性分子式: H2NC(=NH)NH(CH2)3CH(NH2)CO2H

详细说明

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
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。
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
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
按照 cGMP 制造和包装。

Sigma Aldrich - A92406

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。

Sigma Aldrich - W381918

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
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
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。

参考文献

• 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