N-Acetyl-L-leucine

HCID 70912CAS 1188-21-2

基本情報

標準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
単同位体質量: 173.10519334

概要

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.

名称と識別子

優先名称: N-Acetyl-L-leucine
IUPAC: (2S)-2-acetamido-4-methylpentanoic acid

名称と別名

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

名称をさらに表示

E915HL7K2ONSC-206316ACETYLLEUCINE, (S)-CHEBI:17786RefChem:927004DTXCID00209990214-706-3DTXSID40859594

データベース識別子

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

物性

構造計算による物性

XLogP: 0.5
極性表面積: 66.4 Å²
水素結合供与体数: 2
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: 177

実験および物理化学的性質

LogP0.79

Solubility8.1 mg/mL at 25 °C

Human Drugs · 3 件

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine (Orphan designations)

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

Collision Cross Section · 3 件

140.5 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

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

150.1 Å² [M+Na]+

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (91.9%)

化学と産業

薬理情報

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 件

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 件

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