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
展开更多名称
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
- 形式电荷
- 0
- 复杂度
- 177
实验与物化性质
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine (Orphan designations)
FDA approved drugs -> Active ingredient
Collision Cross Section
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
- 溶解度
- DMSO (Slightly), Ethanol (Slightly), Water (Slightly, Heated)
- 酸度系数(pKa)
- 3.67 · 3.67±0.10(Predicted)
- 形态
- Crystalline Powder
- 颜色
- White
- 水溶解性
- 0.81 g/100 · 0.81 g/100 mL (20 ºC)
- BRN
- 1724849 · 1724849
- 主要应用
- peptide synthesis
- InChI
- 1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t7-/m0/s1
- InChIKey
- WXNXCEHXYPACJF-ZETCQYMHSA-N
- SMILES
- CC(C)C[C@H](NC(C)=O)C(O)=O
- CAS 数据库
- 1188 · 1188-21-2(CAS DataBase Reference)
- NIST化学物质信息
- L-leucine, n-acetyl-(1188-21-2)
- EPA化学物质信息
- L-Leucine, N-acetyl- (1188-21-2)
安全与法规
GHS分类
GHS Classification
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
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
- 危险品标志
- Xi
- 危险类别码
- 36/37/38
化学与工业
药理信息
Mechanism of Action
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.
FDA Pharmacological Classification
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
Absorption, Distribution and Excretion
The Cmaxand AUC0-24h of levacetylleucine following oral administration were 8.3 μg/mL and 33.2 h*μg/mL, respectively. The time to maximum concentration (Tmax) is approximately 1 hour.
The apparent volume of distribution following oral administration of levacetylleucine is 253 liters.
The apparent oral clearance of levacetylleucine is 139 L/h.
用途与制造
应用领域
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
上游原料
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
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