P. aeruginosa Metabolome Database: N-Butanoyl-D-homoserine lactone (PAMDB100077)

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

PAMDB100077

Identification

Name:

N-Butanoyl-D-homoserine lactone

Description:

N-Butanoyl-D-homoserine lactone (C4-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:

• (+)-a(S)-butyr-amido-r-butyrolactone

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

• N-[(3S)-2-Oxotetrahydro-3-furanyl]butanamid [German] [ACD/IUPAC Name]

• N-[(3S)-2-Oxotetrahydro-3-furanyl]butanamide [ACD/IUPAC Name]

• N-[(3S)-2-Oxotétrahydro-3-furanyl]butanamide [French] [ACD/IUPAC Name]

• N-[(3S)-2-oxotetrahydrofuran-3-yl]butanamide

• (S)-N-(2-oxo-tetrahydrofuran-3-yl)butyramide

• (S)-N-(2-Oxotetrahydrofuran-3-yl)butyramide

• [67605-85-0] • 67605-85-0 [RN]

• butanamide, N-(tetrahydro-2-oxo-3-furanyl)-, S-

• C4-HSL • C4-HSL| N-(2-Oxotetrahydro-3-furanyl)butanamide

• MFCD12912262 [MDL number]

• N-(2-Oxotetrahydro-3-furanyl)butanamide [ACD/IUPAC Name]

• N-[(3S)-tetrahydro-2-oxo-3-furanyl]-butanamide

• N-[(3S)-tetrahydro-2-oxo-3-furanyl]-butanamide-3,3,4,4,4-d5

• N-butanoylhomoserine lactone

• N-Butanoyl-L-homoserine lactone

• N-butyryl-L-Homoserine lactone

• N-butyryl-L-Homoserine lactone-d5

Chemical Formula:

C₈H₁₃NO₃

Average Molecular Weight:

171.194

Monoisotopic Molecular Weight:

171.089539

InChI Key:

VFFNZZXXTGXBOG-LURJTMIESA-N

InChI:

InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1

CAS number:

Not Available

IUPAC Name:

N-[(3S)-2-oxooxolan-3-yl]butanamide

Traditional IUPAC Name:

Not Available

SMILES:

CCCC(=O)N[C@H]1CCOC1=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
Acyl-l-homoserine lactone
Fatty amide
Gamma butyrolactone
N-acyl-amine
Fatty acyl
Oxolane
Secondary carboxylic acid amide
Lactone
Carboxylic acid ester
Carboxamide group
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Fatty acyl homoserine lactones (C11837)

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Soluble in Cholorform

Predicted Properties

Property	Value	Source
Water Solubility	1.401e⁵	EPIsuite
logP	0.06	ChemAxon
logS		ALOGPS
pKa (Strongest Acidic)		ChemAxon
pKa (Strongest Basic)		ChemAxon
Physiological Charge		ChemAxon
Hydrogen Acceptor Count		ChemAxon
Hydrogen Donor Count		ChemAxon
Polar Surface Area	55.40 Å2	ChemAxon
Solvent Accessible surface area	276.27	ChemAxon
Rotatable Bond Count	3	ChemAxon
Molar Refractivity	42.6 cm3	ACD/Labs
Polarizability	16.9 10-24cm3	ACD/Labs
Density	1.1 g/cm3	ACD/Labs
Boiling point	428.1°C at 760 mmHg
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule		ChemAxon
Lead likeness	Yes	ChemAxon
Muegge Filter	No	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	443433
Chemspider	8305680

N-Butanoyl-D-homoserine lactone (PAMDB100077)

Structure for N-Butanoyl-D-homoserine lactone (PAMDB100077)

Structure for
N-Butanoyl-D-homoserine lactone
(PAMDB100077)