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

• ChemBase ID: 154105
• Molecular Formular: C14H23NO4
• Molecular Mass: 269.33672
• Monoisotopic Mass: 269.16270822
• SMILES: CCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• Canonical SMILES: CCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• InChI: InChI=1S/C14H23NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h12H,2-10H2,1H3,(H,15,17)/t12-/m0/s1
• InChIKey: KYGIKEQVUKTKRR-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]decanamide
• IUPAC Traditional name: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]decanamide
• Synonyms: N-(3-Oxodecanoyl)-L-homoserine lactone

Database IDs

• MDL Number: MFCD12912432
• PubChem SID: 162248244
• PubChem CID: 10221060

CALCULATED PROPERTIES

• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• Acid pKa: 10.296827
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.0628824
• LogD (pH = 7.4): 2.06234
• Log P: 2.0628893
• Molar Refractivity: 70.3851 cm^3
• Polarizability: 27.87623 Å^3
• Polar Surface Area: 72.47 Å^2

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Shipped in: wet ice
• Empirical Formula (Hill Notation): C14H23NO4

DETAILS

Sigma Aldrich - O9014

Biochem/physiol Actions
Acyl homoserine lactone used as an autoinducer of quorum signaling by Pseudomonas putida, Yersinia enterocolitica, and other Gram-negative bacteria.1
N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL) is among a group of homoserine lactones that includes; N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-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.