Structure via PubChem · Public domain (PubChem)
enterobactin
Sign in to saveAlso known as (3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide), H6ent
Enterobactin (also known as enterochelin) is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.
Chemical data
- Formula
- C30H27N3O15
- Molecular weight
- 669.5 g/mol
- 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
- 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
- InChIKey
- SERBHKJMVBATSJ-BZSNNMDCSA-N
- XLogP
- 2.3
- Polar surface area
- 288 Ų
- H-bond donors
- 9
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,076 papers- Enterobactin inhibits microbiota-dependent activation of AhR to promote bacterial sepsis in mice.Nature microbiology · 2025
- Enterobactin: A key player in bacterial iron acquisition and virulence and its implications for vaccine development and antimicrobial strategies.Virulence · 2025
- Enterobactin: an archetype for microbial iron transport.Proceedings of the National Academy of Sciences of the United States of America · 2003
- Siderophore-mediated iron acquisition by Klebsiella pneumoniae.Journal of bacteriology · 2024
- Three paradoxes of ferric enterobactin uptake.Frontiers in bioscience : a journal and virtual library · 2003
via PubMed
Wikidata facts
- Subclass of
- siderophore
- Mass
- 669.144
Show 4 more facts
- chemical formula
- C₃₀H₂₇N₃O₁₅
- 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
- 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
- subject has role
- siderophore
via Wikidata · CC0
~4 min read
Encyclopedic overview
4 sectionsContents
- Structure and biosynthesis
- Mechanism
- History
- References
Enterobactin (also known as enterochelin) is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.
Enterobactin is the strongest siderophore known, binding to the ferric ion (Fe3+) with affinity K = 1052 M−1. This value is substantially larger than even some synthetic metal chelators, such as EDTA (Kf,Fe3+ ~ 1025 M−1). Due to its high affinity, enterobactin is capable of chelating even in environments where the concentration of ferric ion is held very low, such as within living organisms. Pathogenic bacteria can steal iron from other living organisms using this mechanism, even though the concentration of iron is kept extremely low due to the toxicity of free iron.
Excerpted from Wikipedia’s “enterobactin” article, available under the CC BY-SA 4.0 licence.