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Protonated arginine

HCID 28782
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
104352-01-4
標準SMILES
NC(N)=[NH+]CCC[C@H](N)C(=O)[O-]
InChIKey
ODKSFYDXXFIFQN-BYPYZUCNSA-N
分子式
C6H14N4O2
平均分子量
174.2 g/mol
単同位体質量
174.1116757

概要

An essential amino acid that is physiologically active in the L-form.

名称と識別子

優先名称
Protonated arginine
IUPAC
(2S)-2-amino-5-(diaminomethylideneazaniumyl)pentanoate
英語名
2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol, polymer with ethyl 2-propenoate and 2-propenoic acid
分子量
0

名称と別名

CPSSProtonated arginineARGININE, CONJUGATE MONOACID, L-17806-42-7104352-01-4DTXSID201031042L-Arginine, conjugate acid (1:1)2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol, polymer with ethyl 2-propenoate and 2-propenoic acid

データベース識別子

CAS
104352-01-4、17806-42-7、74-79-3
PubChem CID
28782
DTXSID
DTXSID201031042

物性

構造計算による物性

XLogP
-3.5
極性表面積
132 Ų
水素結合供与体数
4
水素結合受容体数
3
回転可能結合数
4
重原子数
12
形式電荷
0
複雑度
171

実験および物理化学的性質

LogP-4.20
Solubility182 mg/mL at 25 °C
Melting Point222 °C
Physical DescriptionSolid
Dissociation Constants2.24 (at 0 °C)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

危険有害性情報

Regulatory InformationChemical: 2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol, polymer with ethyl 2-propenoate and 2-propenoic acid
Other Safety InformationIMAP assessments - 2-Propenoic acid, 2-methyl-, monoester with 1,2-propanediol, polymer with ethyl 2-propenoate and 2-propenoic acid: Human health tier I assessment

化学と産業

薬理情報

Pharmacodynamics · 1 件

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.

Mechanism of Action · 1 件

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 (O2) 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.

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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
Metabolism/MetabolitesSome 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, Distribution and ExcretionAbsorbed from the lumen of the small intestine into the enterocytes. Absorption is efficient and occurs by an active transport mechanism.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency