(2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid

• ChemBase编号: 74848
• 分子式: C6H13NO3
• 平均质量: 147.17232
• 单一同位素质量: 147.08954328
• SMILES: CC(O)[C@H](C)[C@H](N)C(=O)O
• Canonical SMILES: CC([C@@H]([C@@H](C(=O)O)N)C)O
• InChI: InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4?,5-/m0/s1
• InChIKey: OSCCDBFHNMXNME-DSDZBIDZSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid
• IUPAC传统名: (2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid
• 别名: 4-Hydroxy-L-isoleucine; (2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoic acid; 4-HYDROXYISOLEUCINE; HIL; (4S)-4-Hydroxy-L-isoleucine; (2S,3R)-2-Amino-4-hydroxy-3-methylpentanoic acid; 4-Hydroxy-L-isoleucine

登记号

• CAS号: 781658-23-9; 55399-93-4
• MDL号: MFCD06799350
• Beilstein号: 4128096
• PubChem SID: 162039766
• PubChem CID: 2773624

理论计算性质

• Acid pKa: 2.4603202
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -2.9314756
• LogD (pH = 7.4): -2.9373093
• Log P: -2.9314218
• 摩尔折射率: 35.7416 cm^3
• 极化性: 14.5027485 Å^3
• 极化表面积: 83.55 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 闪点: 147 °C; 296.6 °F
• 比旋光度: [α]/D +31.0±1.5°, c = 1 in H2O; [α]/D +34.0±2.0°, c = 1 in H2O

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (TLC)
• 生物来源: from fenugreek seed
• Empirical Formula (Hill Notation): C6H13NO3

详细说明

Sigma Aldrich - 50118

Biochem/physiol Actions
(4S)-4-Hydroxy-L-isoleucine (HIL) is a non-proteinogenic α amino acid produced by the activity of bacterial isoleucine dioxygenase(s). (2S,3R,4S)-HIL is being studied to understand its insulinotropic (anti-diabetic) and anti-obesity effects.
4-Hydroxyisoleucine (HIL) from fenugreek (Trigonella foenum-graecum) seeds is a potential insulinotropic (anti-diabetic) and anti-obesity amino acid. HIL stimulates glucose-dependent insulin secretion from pancreatic cells. HIL activates insulin receptor substrate-associated phosphoinositide 3 (PI3) kinase activity. HIL reduces plasma levels of triglycerides, free fatty acids and cholesterol.

Sigma Aldrich - 49549

Biochem/physiol Actions
A peculiar amino acid extracted from fenugreek seeds and never found in mammalian tissues, exhibits interesting insulinotropic activity; effects on insulin secretion1, plant-derived treatment for metabolic syndrome2.