N-アセチル-L-ロイシン
N-Acetyl-L-leucine
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基本情報
- CAS
1188-21-2- 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
- 現地名
- N-アセチル-L-ロイシン
- 英語名
- N-Acetyl-L-leucine
- 分子式
- C8H15NO3
- 分子量
- 173.21
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
N-アセチル-L-ロイシンN-アセチルロイシン(S)-2-(アセチルアミノ)-4-メチルペンタン酸N‐アセチル‐L‐ロイシン(S)-2-アセトアミド-4-メチルペンタン酸N-アセチル-L-(-)-ロイシンレバセチルロイシンレブアセチルロイシン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
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補完中
- XLogP
- 0.5
- 極性表面積
- 66.4 Ų
- 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
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine (Orphan designations)
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
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]+
物理化学的性質
- 融点
- 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)
- 比重(密度)
- 1.1599 · 1.1599 (rough estimate)
- 屈折率
- -22 ° · -22 ° (C=5, EtOH)
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- DMSO(微量)、エタノール(微量)、水(微量、加温)
- 外見
- 結晶性粉末
- 酸解離定数(Pka)
- 3.67 · 3.67±0.10(Predicted)
- 色
- 白い
- 水溶解度
- 0.81 g/100mL · 0.81g/100mL(20℃)
- BRN
- 1724849 · 1724849
- 主な用途
- ペプチド合成
- 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 データベース
- 1188 · 1188-21-2(CAS DataBase Reference)
- NISTの化学物質情報
- L-leucine, n-acetyl-(1188-21-2)
- EPAの化学物質情報
- L-Leucine, N-acetyl- (1188-21-2)
化学的性質
化学的特性White crystalline powder
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (91.9%)
安全データ
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29241900
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- hazard_class
- IRRITANT
- ストレージクラス
- 11 - Combustible Solids
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
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
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.
用途と製造
General Manufacturing InformationL-Leucine, N-acetyl-: ACTIVE
応用分野
用途有機合成原料。
上流・下流製品情報
上流原料
補足説明
定義ChEBI: The N-acetyl derivative of L-leucine.
関連反応
29 件
化合物ノート
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