3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide

• ChemBase编号: 5947
• 分子式: C16H27NO4
• 平均质量: 297.38988
• 单一同位素质量: 297.19400835
• SMILES: CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• Canonical SMILES: CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• InChI: InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1
• InChIKey: PHSRRHGYXQCRPU-AWEZNQCLSA-N

名称和登记号

名称

• IUPAC标准名: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
• IUPAC传统名: 3-oxo-C12-hsl; 3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
• 别名: 3-Oxo-C12-HSL; N-(3-Oxododecanoyl)-L-homoserine lactone; N-3-OXO-DODECANOYL-L-HOMOSERINE LACTONE

登记号

• MDL号: MFCD08275140
• PubChem SID: 99444795; 160969372
• PubChem CID: 3246941

理论计算性质

JChem

• Acid pKa: 10.296827
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.9520197
• LogD (pH = 7.4): 2.9514773
• Log P: 2.9520266
• 摩尔折射率: 79.5871 cm^3
• 极化性: 31.542976 Å^3
• 极化表面积: 72.47 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.9
• LOG S: -3.8
• 溶解度: 4.75e-02 g/l

分子性质

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 运输包装: wet ice
• Empirical Formula (Hill Notation): C16H27NO4

详细说明

DrugBank - DB08324

Drug information: experimental

Sigma Aldrich - O9139

Biochem/physiol Actions
Acyl homoserine lactone that is an autoinducer of quorum sensing by Pseudomonas aeruginosa.1 Degraded by paraoxonase (PON) family members.2
N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL) is among a group of homoserine lactones that includes; N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.