N-Acetyl-L-leucine

HCID 70912CAS 1188-21-2

기본 정보

표준 SMILES: CC(=O)N[C@@H](CC(C)C)C(=O)O
InChIKey: WXNXCEHXYPACJF-ZETCQYMHSA-N
분자식: C8H15NO3
평균 분자량: 173.21 g/mol
단동위원소 질량: 173.10519334

개요

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.

이름 및 식별자

우선 이름: N-Acetyl-L-leucine
IUPAC: (2S)-2-acetamido-4-methylpentanoic acid

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 0.5
극성 표면적: 66.4 Å²
수소 결합 공여자 수: 2
수소 결합 수용자 수: 3
회전 가능 결합 수: 4
무거운 원자 수: 12
형식 전하: 0
복잡도: 177

실험 및 물리화학적 성질

LogP0.79

Solubility8.1 mg/mL at 25 °C

Human Drugs · 3건

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine (Orphan designations)

FDA approved drugs -> Active ingredient

Physical DescriptionSolid

Collision Cross Section · 3건

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]+

안전 및 규제

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Hazard Classes and CategoriesSkin Irrit. 2 (91.9%)

화학 및 산업

약리 정보

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 · 1건

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 · 6건

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