P. aeruginosa Metabolome Database: 3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide (PAMDB100079)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB100079

Identification

Name:

3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide

Description:

3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide (3-oxo-C12-HSL) is a member N-acyl-homoserine family of small diffusible quorum sensing molecules. N-acyl-homoserine lactones (AHLs) are quorum sensing molecules that control gene expression that is dependent on cell density in many gram-negative bacteria. AHLs are involved in virulence gene regulation, biofilm formation, and some are potent chemoattractants for human immune cells such as neutrophils.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

• 3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamid [German][ACD/IUPAC Name]

• 3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide [ACD/IUPAC Name]

• 3-Oxo-N-(2-oxotétrahydro-3-furanyl)dodécanamide [French] [ACD/IUPAC Name]

• Dodecanamide, 3-oxo-N-(tetrahydro-2-oxo-3-furanyl)- [ACD/Index Name]

• 152833-54-0 [RN]

• 168982-69-2 [RN]

• 3-oxo-C12-AHL

• 3-oxo-C12-HSL

• 3-oxo-N-(2-oxotetrahydrofuran-3-yl)dodecanamide

• 3-Oxo-N-(tetrahydro-2-oxo-3-furanyl)dodecanamide

• N-(3-ketododecanoyl)homoserine lactone

• N-(3-Oxodecanoyl)homoserine lactone

• N-(3-Oxododecanoyl)homoserine lactone

• N-3-oxo-dodecanoyl-L-Homoserine lactone

• PA Autoinducer

• Pseudomonas aeruginosa autoinducer

Chemical Formula:

C₁₆H₂₇NO₄

Average Molecular Weight:

297.39

Monoisotopic Molecular Weight:

297.194

InChI Key:

PHSRRHGYXQCRPU-UHFFFAOYSA-N

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)

CAS number:

Not Available

IUPAC Name:

3-oxo-N-(2-oxooxolan-3-yl)dodecanamide

Traditional IUPAC Name:

Not Available

SMILES:

CCCCCCCCCC(=O)CC(=O)NC1CCOC1=O

Chemical Taxonomy

Taxonomy Description

This 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 Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino 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
Beta-hydroxy ketone
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboximidic acid
Carboximidic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl homoserine lactone (CHEBI:29639)
Fatty acyl homoserine lactones (C11840)
an acyl-homoserine lactone (CPD-10783)

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	107.2 mg/L	EPIsuite
logP	2.95	ChemAxon
logP
logS		ALOGPS
pKa (Strongest Acidic)		ChemAxon
pKa (Strongest Basic)		ChemAxon
Physiological Charge		ChemAxon
Hydrogen Acceptor Count		ChemAxon
Hydrogen Donor Count		ChemAxon
Polar Surface Area	72.47 Å2	ChemAxon
Solvent Accessible surface area	519.48	ChemAxon
Rotatable Bond Count	11	ChemAxon
Molar Refractivity	79.8 cm3	ACD/Labs
Polarizability	31.6 10-24cm3	ACD/Labs
Density	1.1 g/cm3	ACD/Labs
Boiling point	519.4°C at 760 mmHg
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule		ChemAxon
Lead likeness	No	ChemAxon
Muegge Filter	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

Pathways:

Spectra

Spectra:

Not Available

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
PubChem	3246941
Chemspider	113405

3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide (PAMDB100079)

Structure for 3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide (PAMDB100079)

Structure for
3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide
(PAMDB100079)