N-乙酰-L-亮氨酸

N-Acetyl-L-leucine

HCID 70912CAS 1188-21-2

基本信息

标准SMILES
CC(=O)N[C@@H](CC(C)C)C(=O)O
InChIKey
WXNXCEHXYPACJF-ZETCQYMHSA-N
分子式
C8H15NO3
平均分子量
173.21 g/mol
单同位素质量
173.10519334

概述

N-acetyl-L-leucine is the N-acetyl derivative of L-leucine. It has a role as a metabolite. It is a N-acetyl-L-amino acid and a L-leucine derivative. It is a conjugate acid of a N-acetyl-L-leucinate. It is an enantiomer of a N-acetyl-D-leucine.

名称与标识

首选名称
N-Acetyl-L-leucine
IUPAC
(2S)-2-acetamido-4-methylpentanoic acid
中文名
N-乙酰-L-亮氨酸
英文名
N-Acetyl-L-leucine
分子式
C8H15NO3
分子量
173.21

名称与别名

N-Acetyl-L-leucine1188-21-2N-AcetylleucineL-Acetylleucine(S)-2-Acetamido-4-methylpentanoic acidN-acetyl-leucineLevacetylleucine(2S)-2-acetamido-4-methylpentanoic acidLeucine, N-acetyl-, L-N-ACETYL-L-(-)-LEUCINEn-acetyl leucineAQNEURSA
展开更多名称
乙酰-L-亮氨酸N-乙酰-L-亮氨酸N-乙酰-L-白氨酸N-乙酰基-L-亮氨酸RSYY(阿哌沙班)-35N-乙酰-L-亮氨酸标准品N-乙酰-L-亮氨酸,99%N-乙酰-L(DL)-亮氨酸N-乙酰-L-亮氨酸,98%N-乙酰-L/D/DL-色氨酸AC-LEU-OHACETYL-L-LEUCINEACETYL-DL-LEUCINEAC-DL-LEU-OHN-Ac-L-Leu-OHAc-L-Leu-OHn-acetyl-l-leucin(S)-N-Acetylleucine
E915HL7K2ONSC-206316ACETYLLEUCINE, (S)-CHEBI:17786RefChem:927004DTXCID00209990214-706-3DTXSID40859594

数据库标识

CAS
1188-21-2、99-15-0
PubChem CID
70912
DTXSID
DTXSID6045870
ChEMBL
CHEMBL56021
ChEBI
CHEBI:17786
UNII
E915HL7K2O
EC Number
214-706-3
Nikkaji
J23.189D

性质

结构计算性质

XLogP
0.5
极性表面积
66.4 Ų
氢键供体
2
氢键受体
3
可旋转键
4
重原子
12

实验与物化性质

LogP0.79
Solubility8.1 mg/mL at 25 °C
Human Drugs · 3 条

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine (Orphan designations)

FDA approved drugs -> Active ingredient

Physical DescriptionSolid
Collision Cross Section · 3 条

140.5 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

160.24 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150.1 Ų [M+Na]+

物理化学性质

熔点
187 · 187-190 °C(lit.)
比旋光度
-24.5 · -24.5 º (c=4, MeOH)
沸点
303.86 °C · 303.86°C (rough estimate)
密度
1.1599 · 1.1599 (rough estimate)
折射率
-22 ° · -22 ° (C=5, EtOH)
储存条件
Sealed in dry,Room Temperature

安全与法规

GHS分类

GHS Classification · 5 条

This chemical does not meet GHS hazard criteria for 5.4% (2 of 37) of reports.

Warning

H315 (91.9%): 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 37 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危害信息

Hazard Classes and CategoriesSkin Irrit. 2 (91.9%)

安全数据

wgk
3
tsca
TSCA listed
危险等级
IRRITANT
存储类别
11 - Combustible Solids
安全说明
24/25-36-26
海关编码
29241900

化学与工业

药理信息

ATC CodeN - Nervous system
PharmacodynamicsThe pharmacodynamics of levacetylleucine are not well characterized. There does not appear to be a relationship between increasing levacetylleucine exposure and clinical efficacy.
Mechanism of Action · 1 条

Following oral administration, levacetylleucine is taken up via ubiquitously expressed monocarboxylate transporters and distributed to all body tissues. It enters enzyme-controlled pathways that correct metabolic dysfunction and improves adenosine triphosphate (ATP) energy production. The normalization of energy metabolism ameliorates mitochondrial and lysosomal dysfunction and leads to a reduction in the storage of unesterified cholesterol and sphingolipids. Levacetylleucine has also been shown to normalize neuronal membrane potentials in a guinea pig model, thereby improving cellular signaling processes and restoring and protecting neuronal circuits. The specific molecular target of levacetylleucine in the context of Niemann-Pick disease type C (NPC) is unknown.

Biological Half-LifeThe half-life of levacetylleucine is approximately 1 hour.
Metabolism/MetabolitesLevacetylleucine is metabolized into acetate and L-leucine by ubiquitously expressed enzymes.
FDA Pharmacological Classification · 6 条

E915HL7K2O

LEVACETYLLEUCINE

Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors

Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors

Mechanisms of Action [MoA] - Bile Salt Export Pump Inhibitors

Mechanisms of Action [MoA] - Organic Anion Transporter 1 Inhibitors

用途与制造

General Manufacturing InformationL-Leucine, N-acetyl-: ACTIVE
应用领域 · 3 条

简介N-乙酰-L-亮氨酸为白色或类白色结晶性粉末,溶于水,其主要用作有机中间体。

用途N-乙酰-L-亮氨酸为重要的精细有机化工中间体,广泛应用于医药、农药、化学工业等领域。

用途用作生化试剂。

制备方法

合成方法在反应容器中加入2mol的亮氨酸,3-3.5mol的对氯乙酰苯胺,3-4mol的苯乙酰,升高溶液温度至60-65℃,回流80-110min,静置2-3h,降低溶液温度至10-15℃,冷却结晶,过滤晶体,溴化钾溶液洗涤,三乙胺溶液洗涤,硝基甲烷溶液洗涤,脱水剂脱水,得成品N-乙酰-L-亮氨酸。

上下游产品信息

试剂价格

L13926 · 25g
N-乙酰-L-亮氨酸, 99%N-Acetyl-L-leucine, 99% — 667元
34701 · 5g
N-乙酰-L-亮氨酸N-Acetyl-L-leucine, 99% — 451元

供应商50 家

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
甘肃省百事兴药业有限公司15008395229 15008395229 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

相关反应

29 条

关联笔记

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