N-butiril-L-homoserina lactona - Moligand™,≥98% , CAS No.67605-85-0

CAS: 67605-85-0 Cat. No.: N336049 Peso molecular: 171.19

GRADE & PURITY Moligand™, ≥98%

Synonyms

N-(butyryl)-L-homoserine lactone | C4-HSL | SR-01000946805 | C4-HSL;N-Butyryl-L-homoserine lactone | N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide | PAI-1-2 | DTXSID30435962 | SB84058 | SY038520 | N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]BUTANAMIDE | SCHEMBL1319

Storage

Conservar a -20°C

Shipped In

Hielera + almohadillas de hielo

Descripción general

N-butiril-L-homoserina lactona, la detección del quórum es un sistema regulador utilizado por las bacterias para controlar la expresión de genes en respuesta al aumento de la densidad celular. El control de las infecciones bacterianas mediante el apagado de sus sistemas de detección de quórum es un prometedor campo de estudio. La expresión de genes diana específicos, como los reguladores transcripcionales pertenecientes a la familia de proteínas LuxIR, se coordina mediante la síntesis de moléculas difusibles de acilhomoserina lactona (AHL). La N-butiril-L-homoserina lactona es una pequeña molécula de señalización difusible que interviene en la detección del quórum, el control de la expresión génica y el metabolismo celular. Las diversas aplicaciones de esta molécula incluyen la regulación de la virulencia en general, la prevención de infecciones y la formación de biopelículas.

Specifications

Sinónimos

N-(butyryl)-L-homoserine lactone | C4-HSL | SR-01000946805 | C4-HSL;N-Butyryl-L-homoserine lactone | N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide | PAI-1-2 | DTXSID30435962 | SB84058 | SY038520 | N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]BUTANAMIDE | SCHEMBL1319

Especificaciones y pureza

Moligand™, ≥98%

Condiciones de almacenamiento de almacenamiento

Conservar a -20°C

Enviado en

Hielera + almohadillas de hielo

Grado

Moligand™

Tipo de acción

INHIBITOR

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504765265
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765265
• Sonrisas canónicas: CCCC(=O)NC1CCOC1=O
• IUPAC Name: N-[(3S)-2-oxooxolan-3-yl]butanamide
• InChIKey: VFFNZZXXTGXBOG-LURJTMIESA-N
• 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
• Isómeros SMILES: CCCC(=O)N[C@H]1CCOC1=O
• Peso molecular: 171.19
• Reaxy-Rn: 6375
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6375&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase 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
• Clase: 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 Oxolanes Secondary carboxylic acid amides Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives 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 - 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
• Descripción: 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

Objetivos asociados (no humanos)

Clostridioides difficile (2968 Activities)

Explore this target

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

P388 (20296 Activities)

Explore this target

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

rhlA Rhamnosyltransferase 1 subunit A (60 Activities)

Discover Target: rhlA

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in water (10 mg/ml at 25° C), ethanol, DMSO (~30 mg/ml), DMF (~30 mg/ml), and PBS(pH 7.2) (~10 mg/ml).
• Índice de refracción: n20D1.48
• Punto de ebullición (°C): 428.06° C at 760 mmHg
• Punto de fusión (°C): 119.53° C (Predicted)
• Peso molecular: 171.190 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 171.09 Da
• Monoisotopic Mass: 171.09 Da
• Topological Polar Surface Area: 55.400 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 191.000
• 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

Referencias

1. Liushen Lu, Junwei Wang, Ting Qin, Kai Chen, Jun Xie, Bingwen Xi.  (2023)  Carvacrol Inhibits Quorum Sensing in Opportunistic Bacterium Aeromonas hydrophila.  Microorganisms,  11  (8): (2027).  [PMID:37630587] [10.3390/microorganisms11082027]

2. Siyi Chen, Ziang Kong, Liwei Qiu, Han Wang, Qun Yan.  (2024)  Effects of different quorum sensing signal molecules on alleviation of ammonia inhibition during biomethanation.  ENVIRONMENTAL RESEARCH,      [PMID:39505134] [10.1016/j.envres.2024.120295]

3. Na Chen, Jing Xi, Na Du, Ruichen Shen, Rui Zhao, Wei He, Tianhuang Peng, Yanbing Yang, Yun Zhang, Lilei Yu, Weihong Tan, Quan Yuan.  (2024)  Framework nucleic acid strategy enables closer microbial contact for programming short-range interaction.  Science Advances,  10  (50):   [PMID:39661693] [10.1126/sciadv.adr4399]

4. Cheng Qu, Yuchuang Geng, Zhongxiang Ding, Yuzhu Li, Hao Jiang, Mengke Su, Honglin Liu.  (2024)  In Situ Spatiotemporal SERS Profiling of Bacterial Quorum Sensing by Hierarchical Hydrophobic Plasmonic Arrays in Agar Medium.  ANALYTICAL CHEMISTRY,      [PMID:38305857] [10.1021/acs.analchem.3c04299]

5. Xiaojuan Tan, Jingjing Xiao, Qianqian Liu, Ting Yang, Dandan Feng, Ruyi Zheng, Liping Luo, Xi Cheng, Dongsheng Du, Minghui Li, Jinwei Zhou, Guoping Zhu.  (2025)  Regulatory roles of an sRNA derived from the 5´ UTR and sequence internal to lapA in Pseudomonas aeruginosa PAO1.  Microbiology Spectrum,      [PMID:40261038] [10.1128/spectrum.01303-24]

6. Qian Zhang, Fu Wei, Shumin Qin, Bixiang Nie, Lin Deng, Zheng Chen, Siyu Hua.  (2026)  Optimizing HN-AD bacteria-Chlorella symbiotic system via QS molecules for biogas slurry treatment.  Journal of Environmental Chemical Engineering,  14  (3): (122219).  [PMID:] [10.1016/j.jece.2026.122219]