N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide

• ChemBase编号: 3885
• 分子式: C12H14N2O2
• 平均质量: 218.25176
• 单一同位素质量: 218.1055277
• SMILES: c1(cc2c(cc1)[nH]cc2CCNC(=O)C)O
• Canonical SMILES: CC(=O)NCCc1c[nH]c2c1cc(O)cc2
• InChI: InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)
• InChIKey: MVAWJSIDNICKHF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide
• IUPAC传统名: ASE; N-acetylserotonin
• 别名: N-Acetyl Serotonin; N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]acetamide; 5-Hydroxy-N-acetyltryptamine; 5-Hydroxymelatonin; N-acetyl-5-hydroxytryptamine; N-acetyl-5-HT; N-Acetylserotonin; Normelatonin; N-Acetyl-5-hydroxytryptamine; N-Acetylserotonin; N-ACETYL-5-HYDROXYTRYPTAMINE

登记号

• CAS号: 1210-83-9
• EC号: 214-916-5
• MDL号: MFCD00005656
• PubChem SID: 24888384; 46507511; 24278209; 160967321
• PubChem CID: 903
• CHEBI ID: 17697
• CHEMBL: 33103
• Chemspider ID: 879
• 医学主题词(MeSH): N-Acetylserotonin
• 维基百科标题: N-Acetylserotonin

理论计算性质

JChem

• Acid pKa: 9.556519
• 质子受体: 2
• 质子供体: 3
• LogD (pH = 5.5): 1.0016807
• LogD (pH = 7.4): 0.9987193
• Log P: 1.0017188
• 摩尔折射率: 61.7976 cm^3
• 极化性: 24.707266 Å^3
• 极化表面积: 65.12 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.98
• LOG S: -2.58
• 溶解度: 5.69e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; ethanol: soluble50 mg/mL; Methanol
• 外观: Tan Solid; white powder
• 熔点: 107-110°C; 120-122 °C(lit.)
• 密度: 1.268 g/mL

安全信息

• 保存条件: 0°C; -20°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... MTNR1A(4543), MTNR1B(4544)

产品相关信息

• 纯度: ≥99% (TLC); 99%
• Empirical Formula (Hill Notation): C12H14N2O2

详细说明

MP Biomedicals - 02154701

(N-Acetylserotonin)

DrugBank - DB04275

Drug information: experimental

Sigma Aldrich - A1824

包装
1 g in poly bottle
100, 250 mg in poly bottle
Biochem/physiol Actions
Immediate precursor of melatonin. It is formed from serotonin and acetyl-CoA in a reaction catalyzed by serotonin N-acetyl transferase, the rate-limiting enzyme in melatonin biosynthesis. This indoleamine is a weak agonist at melatonin receptors, and has moderate effects on G-protein stimulation and inhibition of cAMP accumulation.

Sigma Aldrich - 855480

包装
25, 100, 250 mg in glass bottle

Toronto Research Chemicals - A179160

A metabolite of Melatonin (M215000).

参考文献

• Reiter, R.J., et al.: J. Biomed. Sci., 7, 444 (2000)
• Chen, Z., et al.: Am. J. Physiol, 284, 1618 (2000)
• Barrenetxe, J., et al.: J. Physiol. Biochem., 60, 61 (2000)