N-(3-oxododecanoyl)-L-homoserine lactone (PAMDB100010)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB100010
Identification
Name: N-(3-oxododecanoyl)-L-homoserine lactone
Description:An N-acyl-L-homoserine lactone having 3-oxododecanoyl as the acyl substituent.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3-oxo-C12-AHL
  • 3-oxo-C12-HSL
  • N-(3-ketododecanoyl)-L-homoserine lactone
Chemical Formula: C16H27NO4
Average Molecular Weight: 297.3899
Monoisotopic Molecular Weight: 297.194
InChI Key: PHSRRHGYXQCRPU-AWEZNQCLSA-N
InChI:InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1
CAS number: Not Available
IUPAC Name:3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]dodecanamide
Traditional IUPAC Name: Not Available
SMILES:CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent N-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • N-acyl-alpha amino acid or derivatives
  • Acyl-homoserine lactone
  • Acyl-l-homoserine lactone
  • Fatty amide
  • Gamma butyrolactone
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • N-acyl-amine
  • Tetrahydrofuran
  • Carboxamide group
  • Carboxylic acid ester
  • Ketone
  • Secondary carboxylic acid amide
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
  • N-acyl-L-homoserine lactone, N-(3-oxododecanoyl)homoserine lactone (CHEBI:44534)
  • Fatty acyl homoserine lactones (LMFA08030001)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass297.3894ChemAxon
logP2.9089ChemAxon
H-bond acceptors5ChemAxon
H-bond donors1ChemAxon
Rotatable bonds12ChemAxon
PSA72.4700ChemAxon
RO5 violations0ChemAxon
RO3 violations3ChemAxon
Refractivity81.3987ChemAxon
Atoms48ChemAxon
Rings1ChemAxon
Heavy atoms21ChemAxon
Hydrogen atoms27ChemAxon
Heteroatoms5ChemAxon
N/O atoms5ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms0ChemAxon
Chiral centers1ChemAxon
R/S chiral centers1ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers0ChemAxon
Stereo double bonds0ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds0ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
S-Adenosylmethionine → 5'-Methylthioadenosine + N-(3-oxododecanoyl)-L-homoserine lactone + Hydrogen ion
N-(3-oxododecanoyl)-L-homoserine lactone + Water → L-homoserine lactone + 3-oxo-dodecanoate
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Lawrence RN, Dunn WR, Bycroft B, Camara M, Chhabra SR, Williams P, Wilson VG. The Pseudomonas aeruginosa quorum-sensing signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone, inhibits porcine arterial smooth muscle contraction. Br J Pharmacol. 1999 Oct;128(4):845-8. Pubmed: 10556916
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    LIPID MAPSLMFA08030001