Compound: enterobactin
SMILES: O=C1OC[C@H](NC(=O)c2c(O)c(O)ccc2)C(=O)OC[C@@H](C(OC[C@@H]1NC(=O)c3c(O)c(O)ccc3)=O)NC(=O)c4c(O)c(O)ccc4
InChIKey: SERBHKJMVBATSJ-BZSNNMDCSA-N
Synonyms: enterobactin, 28384-96-5, Enterochelin, 35C9R2N24F, CHEBI:28855, tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester, DTXSID40182617, tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester, Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxy-, (3S-(3R*,7R*,11R*)))-, N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide, N-((3S,7S,11S)-7,11-bis((2,3-dihydroxybenzoyl)amino)-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl)-2,3-dihydroxybenzamide, RefChem:388954, DTXCID80105108, N-((3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)-2,3-dihydroxybenzamide, N-(7,11-bis((2,3-dihydroxybenzoyl)amino)-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl)-2,3-dihydroxybenzamide, MFCD16876395, Enterochellin, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide), Cyclotris(N-2,3-dihydroxybenzoyl-L-seryl), Chymosin preparation, Escherichia coli K-12, N,N',N''-((3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide), N-(2,3-DIHYDROXYBENZOYL)-L-SERINE TRIMOLECULAR CYCLIC ESTER, Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris[2,3-dihydroxy-, [3S-(3R*,7R*,11R*)]-, UNII-35C9R2N24F, 2xuz, H6ent, BENZAMIDE, N,N',N''-((3S,7S,11S)-2,6,10-TRIOXO-1,5,9-TRIOXACYCLODODECANE-3,7,11-TRIYL)TRIS(2,3-DIHYDROXY-, Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxy-, (3S-(3R*,7R*,11R*))-, benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-, EB4, C30H27N3O15, ENTEROBACTIN [MI], SCHEMBL263621, CHEMBL432995, orb1298062, SCHEMBL29427854, SERBHKJMVBATSJ-BZSNNMDCSA-N, GLXC-21659, Enterobactin  from Escherichia coli, DA-73127, FE177921, N,N',N''-((3S,7S,11S)-2,6,10- trioxo-1,5,9-trioxacyclododecane- 3,7,11-triyl)tris(2,3-dihydroxybenzamide), SY253278, HY-128525, 1,5,9-Trioxacyclododecane, benzamide deriv., CS-0095342, C05821, F77042, Q523354, (3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide), Benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy- (9CI), N,N inverted exclamation mark ,N inverted exclamation mark  inverted exclamation mark -[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide), N-(2,3-dihydroxybenzoyl)-O-[N-(2,3-dihydroxybenzoyl)-O-[N-(2,3-dihydroxybenzoyl)-L-seryl]-L-seryl]-L-serine-(3->1(3))-lactone, N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzene)amido]-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide, N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxy-benzamide, o-Pyrocatechuamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris- (8CI), Tri-(N-(2,3-Dihydroxybenzoyl)-L-serine)-ester; N,N',N''-((3S,7S,11S)-2,6,10- trioxo-1,5,9-trioxacyclododecane- 3,7,11-triyl)tris(2,3-dihydroxybenzamide)
Theoretical properties:
molecular_formula: C30H27N3O15
molecular_weight: 669.5 g/mol
exact_mass: 669.14421716 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 9
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 6
heavy_atom_count: 48
topological_polar_surface_area: 288 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Enterobactin is a macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella. It has a role as a siderophore and a bacterial metabolite. It is a macrotriolide, a polyphenol, a member of catechols and a crown compound. It is a conjugate acid of an enterobactin(6-) and an enterobactin(1-).
chebi: A macrotriolide produced by certain members of Enterobacteriaceae, e.g. <em>Escherichia coli</em> and <em>Salmonella</em>.
chembl: ENTEROBACTIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.