Enterobactin - ≥98% , CAS No.28384-96-5

CAS: 28384-96-5 Cat. No.: E693940 Molecular Weight: 669.55

GRADE & PURITY ≥98%

Synonyms

enterobactin | 35C9R2N24F | tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester | DTXSID40182617 | tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester | N-((3S,7S,11S)-7,11-bis((2,3-dihydroxybenzoyl)amino)-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl)-2,3-dihydroxybenzam

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Enterobactin is a siderophore produced by Gram-negative bacteria and has an extremely high affinity for iron. During the process of Salmonella typhimurium infecting macrophages, Enterobactin can not only help bacteria uptake iron but also reduce the antibacterial activity of macrophages. In addition, Enterobactin is also involved in the oxidative stress response of Escherichia coli. Enterobactin can be hydrolyzed by Fes in the cell and exert antioxidant effects by scavenging free radicals.

Application：

Enterobactin has been used: as a positive control in tryptophan fluorescence quenching experiments as a reference standard in high performance liquid chromatography to quantify Kosakonia radicincitans culture medium siderophores in the crystallization reservoir to remove iron contamination in the medium and in Fe-enterbactin binding studies This preparation of enterobactin is not bound to iron and will bind to Fe3+ and Fe2+ in solution.

Biochem/physiol Actions：

Enterobactin is a catechol (a benzenediol, C6H4(OH)2) type iron siderophore produced in small quantities by Escherichia coli and related enteric bacteria when grown on iron deficient media. It is one of the most powerful ferric ion complexing agents known. Iron mobilization and uptake by microbes is mediated by low molecular weight complexing agents named siderophores. Enterobactin is a catechol (a benzenediol, C6H4(OH)2) type siderophore produced in small quantities by Escherichia coli and related enteric bacteria when grown on iron deficient media, and is one of the most powerful ferric ion complexing agents known. Enterobactin is a very effective sequestering agent for iron, able to remove iron from proteins, insoluble iron complexes, and other siderophores. Studies of the chemistry, regulation, synthesis, recognition, and transport of enterobactin make it the best-understood siderophore.

Specifications

Synonyms

enterobactin | 35C9R2N24F | tri-(2, 3-dihydroxy-N-benzoyl-L-serine)-ester | DTXSID40182617 | tri-(N-(2, 3-dihydroxybenzoyl)-L-serine)-ester | N-((3S, 7S, 11S)-7, 11-bis((2, 3-dihydroxybenzoyl)amino)-2, 6, 10-trioxo-1, 5, 9-trioxacyclododec-3-yl)-2, 3-dihydroxybenzam

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Enterobactin is a catechol (a benzenediol, C6H4(OH)2) type iron siderophore produced in small quantities by Escherichia coli and related enteric bacteria when grown on iron deficient media. It is one of the most powerful ferric ion complexing agents known

Storage

Store at -20°C

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

• Canonical Smiles: C1C(C(=O)OCC(C(=O)OCC(C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O
• IUPAC Name: N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide
• InChIKey: SERBHKJMVBATSJ-BZSNNMDCSA-N
• INCHI: 1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1
• Isomeric SMILES: C1[C@@H](C(=O)OC[C@@H](C(=O)OC[C@@H](C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O
• Alternate CAS: 28384-96-5,9001-98-3
• MeSH Entry Terms: Enterobactin;Enterochelin
• Molecular Weight: 669.55

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Depsipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Depsipeptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclic depsipeptides
• Alternative Parents: Alpha amino acid esters N-acyl-alpha amino acids and derivatives Macrolides and analogues Macrolactams Salicylamides Tricarboxylic acids and derivatives Benzamides Catechols Benzoyl derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Vinylogous acids Secondary carboxylic acid amides Lactones Carboxylic acid esters Oxacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Cyclic depsipeptide - Alpha-amino acid ester - N-acyl-alpha amino acid or derivatives - Macrolide - Macrolactam - Alpha-amino acid or derivatives - Salicylic acid or derivatives - Salicylamide - Benzamide - Benzoic acid or derivatives - Tricarboxylic acid or derivatives - Benzoyl - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Carboxamide group - Carboxylic acid ester - Secondary carboxylic acid amide - Lactone - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
• External Descriptors: polyphenol - macrocycle - crown compound - organic aromatic compound

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(Human)

TF Tbio Serotransferrin (88 Activities)

Discover Target: TF

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

Associated Targets(non-human)

Vibrio cholerae (1211 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 669.500 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 669.144 Da
• Monoisotopic Mass: 669.144 Da
• Topological Polar Surface Area: 288.000 Ų
• Heavy Atom Count: 48
• Formal Charge: 0
• Complexity: 1060.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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