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

• ChemBase ID: 5947
• Molecular Formular: C16H27NO4
• Molecular Mass: 297.38988
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
• IUPAC Traditional name: 3-oxo-C12-hsl; 3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
• Synonyms: 3-Oxo-C12-HSL; N-(3-Oxododecanoyl)-L-homoserine lactone; N-3-OXO-DODECANOYL-L-HOMOSERINE LACTONE

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.296827
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.9520197
• LogD (pH = 7.4): 2.9514773
• Log P: 2.9520266
• Molar Refractivity: 79.5871 cm^3
• Polarizability: 31.542976 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.9
• LOG S: -3.8
• Solubility (Water): 4.75e-02 g/l

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Shipped in: wet ice
• Empirical Formula (Hill Notation): C16H27NO4

DETAILS

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.