N-(Ketocaproyl)-L-homoserine Lactone - Moligand™, ≥98% , CAS No.143537-62-6

CAS: 143537-62-6 Cat. No.: N137466 Molecular Weight: 213.23

GRADE & PURITY Moligand™, ≥98%

Synonyms

N-(beta-Ketocaproyl)-L-homoserine lactone | N-(3-Oxohexanoyl)-L-homoserine lactone | N-(beta-Ketocaproyl)-DL-homoserine lactone | (S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)hexanamide | N-(β-Ketocaproyl)-L-homoserine Lactone | N-(β-Ketocaproyl)-L-homoserine L

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

N-(3-Oxohexanoyl)-L-homoserine lactone (OHHL; N-(3-Oxohexanoyl)homoserine lactone) is a specific agonist of LuxR-type transcription factor CarR with a Kd of 1.8 μM. N-(3-Oxohexanoyl)-L-homoserine lactone activates CarR by inducing protein multimerization, promoting its binding to target DNA sequences in the carR-carA intergenic region, thereby upregulating the transcription of carbapenem biosynthesis genes. N-(3-Oxohexanoyl)-L-homoserine lactone acts as a quorum sensing signal molecule, enabling bacteria to coordinate the production of carbapenem antibiotics in a cell density-dependent manner. N-(3-Oxohexanoyl)-L-homoserine lactone is used to study bacterial quorum sensing mechanisms, especially the secondary metabolism and virulence factor regulatory pathways of Erwinia carotovora and Yersinia enterocolitica.

Specifications

Synonyms

N-(beta-Ketocaproyl)-L-homoserine lactone | N-(3-Oxohexanoyl)-L-homoserine lactone | N-(beta-Ketocaproyl)-DL-homoserine lactone | (S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)hexanamide | N-(β-Ketocaproyl)-L-homoserine Lactone | N-(β-Ketocaproyl)-L-homoserine L

Specifications & Purity

Moligand™, ≥98%

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.

Grade

Moligand™

Action Type

MODULATOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCC(=O)CC(=O)NC1CCOC1=O
• IUPAC Name: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide
• InChIKey: YRYOXRMDHALAFL-QMMMGPOBSA-N
• 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
• Isomeric SMILES: CCCC(=O)CC(=O)N[C@H]1CCOC1=O
• WGK Germany: 3
• Molecular Weight: 213.23
• Reaxy-Rn: 13576940
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=13576940&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 1,3-dicarbonyl compounds Tetrahydrofurans Secondary carboxylic acid amides Ketones Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• 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 - 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
• 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: N-acyl-L-homoserine lactone

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)

Agrobacterium tumefaciens (620 Activities)

Explore this target

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

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 ethanol, DMSO (~30 mg/ml), DMF (~30 mg/ml), methanol, and chloroform.
• Sensitivity: Light & Moisture Sensitive；heat sensitive；Air Sensitive
• Molecular Weight: 213.230 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 213.1 Da
• Monoisotopic Mass: 213.1 Da
• Topological Polar Surface Area: 72.500 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 275.000
• 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