N-[(3S)-Tetrahydro-2-oxo-3-furanyl]heptanamide, C7-HSL - ≥98% , CAS No.177158-20-2

CAS: 177158-20-2 Cat. No.: N348009 Molecular Weight: 213.27

GRADE & PURITY ≥98%

Synonyms

N-heptanoyl-L-homoserinelactone | Heptanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]- | Q27110200 | J-011254 | N-Heptanoyl-L-homoserine lactone, >=96% (HPLC) | LMFA08030006 | N-[(3S)-2-oxooxolan-3-yl]heptanamide | FTMZLSDESAOPSZ-VIFPVBQESA-N | N-[(3S)-Tetra

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

N-heptanoyl-L-Homoserine lactone (C7-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism. Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density, and by quenching this system could lead to controlling bacterial infections. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. The diverse applications of this molecule include regulation of virulence, infection prevention, and septicemia in fish.

Specifications

Synonyms

N-heptanoyl-L-homoserinelactone | Heptanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]- | Q27110200 | J-011254 | N-Heptanoyl-L-homoserine lactone, >=96% (HPLC) | LMFA08030006 | N-[(3S)-2-oxooxolan-3-yl]heptanamide | FTMZLSDESAOPSZ-VIFPVBQESA-N | N-[(3S)-Tetra

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

N-Heptanoyl-L-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell commu

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504758804
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758804
• Canonical Smiles: CCCCCCC(=O)NC1CCOC1=O
• IUPAC Name: N-[(3S)-2-oxooxolan-3-yl]heptanamide
• InChIKey: FTMZLSDESAOPSZ-VIFPVBQESA-N
• INCHI: 1S/C11H19NO3/c1-2-3-4-5-6-10(13)12-9-7-8-15-11(9)14/h9H,2-8H2,1H3,(H,12,13)/t9-/m0/s1
• Isomeric SMILES: CCCCCCC(=O)N[C@H]1CCOC1=O
• Molecular Weight: 213.27
• Reaxy-Rn: 10162518
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10162518&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-acyl-alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids and derivatives
• Alternative Parents: Alpha amino acid esters Acyl-L-homoserine lactones N-acyl amines Gamma butyrolactones Tetrahydrofurans Secondary carboxylic acid amides Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• 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 - Tetrahydrofuran - Carboxamide group - Carboxylic acid ester - Lactone - Secondary carboxylic acid amide - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic oxide - Aliphatic heteromonocyclic compound
• 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.
• External Descriptors: Fatty acyl homoserine lactones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

luxR Transcriptional activator protein luxR (400 Activities)

Discover Target: luxR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

traR Transcriptional activator protein traR (147 Activities)

Discover Target: traR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (0.5 mg/ml at 25° C), DMSO (~20 mg/ml), DMF (~20 mg/ml), ethanol, and DMSO:PBS pH 7.2 1:1 (~0.5 mg/ml).
• Refractive Index: n20D1.48 (Predicted)
• Boil Point(°C): ~440.4° C at 760 mmHg (Predicted)
• Melt Point(°C): 143.23° C (Predicted)
• Molecular Weight: 213.270 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 213.136 Da
• Monoisotopic Mass: 213.136 Da
• Topological Polar Surface Area: 55.400 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 228.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1