L-γGlu-S-ニトロソ-L-Cys-Gly-OH

S-Nitrosoglutathione

HCID 104858

基本情報

CAS
57564-91-7
標準SMILES
N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(=O)O)C(=O)O
InChIKey
HYHSBSXUHZOYLX-WDSKDSINSA-N
分子式
C10H16N4O7S
平均分子量
336.32 g/mol
単同位体質量
336.07396985

概要

S-nitrosoglutathione is a glutathione derivative that is glutathione in which the hydrogen attached to the sulfur has been replaced by a nitroso group. It has a role as a bronchodilator agent, a platelet aggregation inhibitor, a nitric oxide donor and a signalling molecule. It is a nitrosothio compound and a glutathione derivative. It is a conjugate acid of a S-nitrosoglutathione(2-).

名称と識別子

優先名称
S-Nitrosoglutathione
IUPAC
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
現地名
L-γGlu-S-ニトロソ-L-Cys-Gly-OH
英語名
S-NITROSOGLUTATHIONE
分子式
C10H16N4O7S
分子量
336.32

名称と別名

57564-91-7gsnoS-nitrosoglutathioneNitrosoglutathioneSNOGGlutathione thionitriteN-(N-L-gamma-Glutamyl-S-nitroso-L-cysteinyl)glycine78RRI89ZTODTXSID1040613Glycine, N-(N-L-gamma-glutamyl-S-nitroso-L-cysteinyl)-RVC 588 (PEPTIDE)(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid
名称をさらに表示
L-γGlu-S-ニトロソ-L-Cys-Gly-OHS-ニトロソ-L-グルタチオンS-ニトロソグルタチオンニトロソグルタチオンγGlu-S-ニトロソ-Cys-Gly-OHN-(N-L-Γ-グルタミル-S-ニトロソ-L-システィニル)グリシン(2S)-2-アミノ-4-{[(1R)-1-[(カルボキシメチル)カルバモイル]-2-(ニトロソスルファニル)エチル]カルバモイル}ブタン酸GNSORVC 588GSNO, SNOGS-NitrosoglutationeS-Nitrosylglutathione
CHEBI:50091(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acidS-Nitroso-GSH(2S)-2-amino-4-(((1R)-1-((carboxymethyl)carbamoyl)-2-(nitrososulfanyl)ethyl)carbamoyl)butanoic acid(2S)-2-amino-5-(((2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl)amino)-5-oxopentanoic acidRefChem:180705DTXCID401526730637-341-5

データベース識別子

CAS
57564-91-7
PubChem CID
104858
DTXSID
DTXSID1040613
ChEMBL
CHEMBL63507
ChEBI
CHEBI:50091
UNII
78RRI89ZTO
EC Number
637-341-5
Nikkaji
J361.904D

物性

構造計算による物性

XLogP
-4.8
極性表面積
214 Ų
水素結合供与体数
5
水素結合受容体数
10
回転可能結合数
10
重原子数
22

実験および物理化学的性質

Physical DescriptionSolid

物理化学的性質

融点
170 °C · >170°C (dec.)
比重(密度)
1.68 · 1.68
屈折率
1.6 · 1.6000 (estimate)
貯蔵温度
-20 °C · -20°C
溶解性
DMSO(微量)、水(微量)
外見
ピンクの固体

化学的性質

化学的特性Pink Powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

wgk
3
rtecs
MC0558000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological Classification · 6 件

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Agents that cause an increase in the expansion of a bronchus or bronchial tubes.

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

Drugs used to cause dilation of the blood vessels.

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

A diverse group of agents, with unique chemical structures and biochemical requirements, which generate NITRIC OXIDE. These compounds have been used in the treatment of cardiovascular diseases and the management of acute myocardial infarction, acute and chronic congestive heart failure, and surgical control of blood pressure. (Adv Pharmacol 1995;34:361-81)

応用分野 · 3 件

説明S-Nitroso-L-glutathione is an S-nitrosothiol NO donor based on naturally-occurring glutathione. It is a potent smooth muscle relaxant and inhibitor of platelet aggregation. Its stability in solution varies from seconds to hours depending on temperature, buffer composition, and metal content.

使用S-Nitrosoglutathione (GSNO) has been used:as a standard in reversed phase chromatography coupled to chemical vapour generation and atomic fluorescence detector (RPC-CVGAFS) and reversed phase chromatography fluorimetric (RPC-FD).as a standard in spectrophotometric and high-performance liquid chromatography (HPLC) assay.

一般的な説明A utility carrier of nitric oxide. Breaks down at physiological pH to produce nitric oxide. Causes smooth muscle relaxation and inhibits platelet aggregation. Induces apoptosis in mouse thymocytes. Note: 1 set = 5 x 2.5 mg.

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関連反応

26 件

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