DL-6,8-チオクタミド

Lipoamide

HCID 863CAS 3206-73-3

基本情報

標準SMILES: NC(=O)CCCCC1CCSS1
InChIKey: FCCDDURTIIUXBY-UHFFFAOYSA-N
分子式: C8H15NOS2
平均分子量: 205.3 g/mol
単同位体質量: 205.0595061

概要

Lipoamide is a monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a monocarboxylic acid amide and a member of dithiolanes. It is functionally related to a lipoic acid.

名称と識別子

優先名称: Lipoamide
IUPAC: 5-(dithiolan-3-yl)pentanamide
現地名: DL-6,8-チオクタミド
英語名: DL-5-(1,2-Dithiolan-3-yl)valeramide
分子式: C8H15NOS2
分子量: 205.34

名称と別名

lipoamide940-69-2Thioctamide5-(1,2-Dithiolan-3-yl)pentanamidethioctic acid amideLipoacindl-6,8-ThioctamideDL-lipoamideLipamideVitamin NLipoamidLipoicin

名称をさらに表示

DL-6,8-チオクタミド(±)-α-リパミドrac-(3R*)-1,2-ジチオラン-3-ペンタンアミド(±)-チオクトアミド(±)-α-リポアミドrac-(R*)-1,2-ジチオラン-3-ペンタンアミドde-チオクト酸アミドDL-a-LipoamideDL-α-LipoamideDL-THIOCTAMIDETHIOCTIC AMIDEDL-α-LipoamideALPHA-LIPOAMIDE6-THIOCTIC AMIDEDL-thioctic amide

Pathoclon1,2-Dithiolane-3-pentanamideThioctamidThiotominThioamiTicolinLypoaranalpha-Lipoic acid amide

データベース識別子

CAS: 3206-73-3、940-69-2
PubChem CID: 863
DTXSID: DTXSID2046541
ChEMBL: CHEMBL1403899
ChEBI: CHEBI:17460
UNII: Q1GT04827L
EC Number: 213-375-2、221-710-9
Nikkaji: J25.390A

物性

構造計算による物性

XLogP: 1
極性表面積: 93.7 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 5
重原子数: 12
形式電荷: 0
複雑度: 152

実験および物理化学的性質

Chemical ClassesOther Classes -> Amides, Other

LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> Primary amides [FA0801]

Melting Point126.0 - 129.0 °C

Physical Description · 2 件

Yellow solid; [Alfa Aesar MSDS]

Solid

Collision Cross Section · 5 件

146.29 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150.4 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

150.5 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

139.3 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150.6 Å² [M+Na]+

物理化学的性質

融点: 127 · 127-129 °C(lit.)
貯蔵温度: 2 · 2-8°C
InChI: InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
InChIKey: FCCDDURTIIUXBY-UHFFFAOYSA-N
SMILES: C(N)(=O)CCCCC1CCSS1
CAS データベース: 3206 · 3206-73-3(CAS DataBase Reference)
NISTの化学物質情報: 1 · 1,2-Dithiolane-3-pentanamide, (.+/-.)-(3206-73-3)

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazards SummaryHarmful by ingestion; [Alfa Aesar MSDS]

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

wgk: 3
rtecs: JP1185000
safety_code: 22-24/25

化学と産業

薬理情報

Tissue LocationsPlacenta

Cellular LocationsMembrane

Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria

応用分野

使用hepatoprotectant

調製方法

純化方法DL--Lipoamide is recrystallised from EtOH and has UV with max 331nm in MeOH. [Reed et al. J Biol Chem 232 143 1958, IR: Wagner et al. J Am Chem Soc 78 5079 1956, Beilstein 19/7 V 238.]