Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H27N3O15 |
| Molecular Weight | 669.5465 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C3=C(O)C(O)=CC=C3)NC(=O)C4=C(O)C(O)=CC=C4)=C1O
InChI
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
| Molecular Formula | C30H27N3O15 |
| Molecular Weight | 669.5465 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Infrared multiphoton dissociation of the siderophore enterobactin and its Fe(III) complex. Influence of Fe(III) binding on dissociation kinetics and relative energetics. | 2007-04 |
|
| Enterohaemorrhagic Escherichia coli O157 and non-O157 serovars differ in their mechanisms for iron supply. | 2007-02 |
|
| Effects of macromolecular crowding on the intrinsic catalytic efficiency and structure of enterobactin-specific isochorismate synthase. | 2007-01-31 |
|
| Blockade of catecholamine-induced growth by adrenergic and dopaminergic receptor antagonists in Escherichia coli O157:H7, Salmonella enterica and Yersinia enterocolitica. | 2007-01-30 |
|
| Evidence of ball-and-chain transport of ferric enterobactin through FepA. | 2007-01-05 |
|
| Endogenous MMTV proviruses induce susceptibility to both viral and bacterial pathogens. | 2006-12 |
|
| Environmental factors influence the production of enterobactin, salmochelin, aerobactin, and yersiniabactin in Escherichia coli strain Nissle 1917. | 2006-12 |
|
| Siderophore-mediated iron transport in Bacillus subtilis and Corynebacterium glutamicum. | 2006-11 |
|
| Facile detection of acyl and peptidyl intermediates on thiotemplate carrier domains via phosphopantetheinyl elimination reactions during tandem mass spectrometry. | 2006-10-24 |
|
| Localized protein interaction surfaces on the EntB carrier protein revealed by combinatorial mutagenesis and selection. | 2006-08-30 |
|
| Microbial evasion of the immune system: structural modifications of enterobactin impair siderocalin recognition. | 2006-08-30 |
|
| Structural characterization of enterobactin hydrolase IroE. | 2006-08-29 |
|
| An [{Fe(mecam)}2]6- bridge in the crystal structure of a ferric enterobactin binding protein. | 2006-08-04 |
|
| Interdomain communication between the thiolation and thioesterase domains of EntF explored by combinatorial mutagenesis and selection. | 2006-08 |
|
| Iron nutrition and physiological responses to iron stress in Nitrosomonas europaea. | 2006-08 |
|
| Bromoenterobactins as potent inhibitors of a pathogen-associated, siderophore-modifying C-glycosyltransferase. | 2006-07-26 |
|
| Nanomolar inhibition of the enterobactin biosynthesis enzyme, EntE: synthesis, substituent effects, and additivity. | 2006-07-15 |
|
| Enterobactin protonation and iron release: structural characterization of the salicylate coordination shift in ferric enterobactin. | 2006-07-12 |
|
| Tren-based analogues of bacillibactin: structure and stability. | 2006-07-10 |
|
| Determination of the crystal structure of EntA, a 2,3-dihydro-2,3-dihydroxybenzoic acid dehydrogenase from Escherichia coli. | 2006-07 |
|
| AgdbNet - antigen sequence database software for bacterial typing. | 2006-06-21 |
|
| Multidrug-resistant commensal Escherichia coli in children, Peru and Bolivia. | 2006-06 |
|
| Catecholate receptor proteins in Salmonella enterica: role in virulence and implications for vaccine development. | 2006-05-01 |
|
| Parasitism of iron-siderophore receptors of Escherichia coli by the siderophore-peptide microcin E492m and its unmodified counterpart. | 2006-04 |
|
| Structure of the EntB multidomain nonribosomal peptide synthetase and functional analysis of its interaction with the EntE adenylation domain. | 2006-04 |
|
| Using pyrosequencing to shed light on deep mine microbial ecology. | 2006-03-20 |
|
| Cereulide synthetase gene cluster from emetic Bacillus cereus: structure and location on a mega virulence plasmid related to Bacillus anthracis toxin plasmid pXO1. | 2006-03-02 |
|
| Putative virulence-related genes in Vibrio anguillarum identified by random genome sequencing. | 2006-03 |
|
| How pathogenic bacteria evade mammalian sabotage in the battle for iron. | 2006-03 |
|
| Enzymatic tailoring of enterobactin alters membrane partitioning and iron acquisition. | 2006-02-17 |
|
| Activity screening of carrier domains within nonribosomal peptide synthetases using complex substrate mixtures and large molecule mass spectrometry. | 2006-02-14 |
|
| Bacillibactin-mediated iron transport in Bacillus subtilis. | 2006-01-11 |
|
| Discovery of a new peptide natural product by Streptomyces coelicolor genome mining. | 2005-10 |
|
| In vitro characterization of salmochelin and enterobactin trilactone hydrolases IroD, IroE, and Fes. | 2005-08-10 |
|
| Functional annotation by identification of local surface similarities: a novel tool for structural genomics. | 2005-08-02 |
|
| Mechanistic and inhibition studies of chorismate-utilizing enzymes. | 2005-08 |
|
| Functions of the siderophore esterases IroD and IroE in iron-salmochelin utilization. | 2005-07 |
|
| The detection of salmochelin and yersiniabactin in uropathogenic Escherichia coli strains by a novel hydrolysis-fluorescence-detection (HFD) method. | 2005-06 |
|
| The Pseudomonas aeruginosa pirA gene encodes a second receptor for ferrienterobactin and synthetic catecholate analogues. | 2005-05-15 |
|
| Reduced hydroperoxidase (HPI and HPII) activity in the Deltafur mutant contributes to increased sensitivity to UVA radiation in Escherichia coli. | 2005-05-13 |
|
| Iron limitation induces SpoT-dependent accumulation of ppGpp in Escherichia coli. | 2005-05 |
|
| Microarray karyotyping of commercial wine yeast strains reveals shared, as well as unique, genomic signatures. | 2005-04-16 |
|
| Genome-wide screen for genes with effects on distinct iron uptake activities in Saccharomyces cerevisiae. | 2005-01 |
|
| Rapid identification of siderophores by combined thin-layer chromatography/matrix-assisted laser desorption/ionization mass spectrometry. | 2005 |
|
| Cell biology: iron thievery. | 2004-12-16 |
|
| Lipocalin 2 mediates an innate immune response to bacterial infection by sequestrating iron. | 2004-12-16 |
|
| Siderophore and haem iron use by Tritrichomonas foetus. | 2004-12 |
|
| Production by Escherichia coli isolates of siderophore and other virulence factors and their pathogenic role in a cutaneous infection model. | 2004-11 |
|
| Prediction of DtxR regulon: identification of binding sites and operons controlled by Diphtheria toxin repressor in Corynebacterium diphtheriae. | 2004-09-24 |
|
| Metal-organic complexation in the marine environment. | 2001-09-28 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:52:11 GMT 2025
by
admin
on
Mon Mar 31 22:52:11 GMT 2025
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| Record UNII |
35C9R2N24F
|
| Record Status |
Validated (UNII)
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| Record Version |
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| Code System | Code | Type | Description | ||
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28384-96-5
Created by
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28855
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77805
Created by
admin on Mon Mar 31 22:52:11 GMT 2025 , Edited by admin on Mon Mar 31 22:52:11 GMT 2025
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DTXSID40182617
Created by
admin on Mon Mar 31 22:52:11 GMT 2025 , Edited by admin on Mon Mar 31 22:52:11 GMT 2025
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m4920
Created by
admin on Mon Mar 31 22:52:11 GMT 2025 , Edited by admin on Mon Mar 31 22:52:11 GMT 2025
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PRIMARY | Merck Index | ||
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Enterobactin
Created by
admin on Mon Mar 31 22:52:11 GMT 2025 , Edited by admin on Mon Mar 31 22:52:11 GMT 2025
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35C9R2N24F
Created by
admin on Mon Mar 31 22:52:11 GMT 2025 , Edited by admin on Mon Mar 31 22:52:11 GMT 2025
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34231
Created by
admin on Mon Mar 31 22:52:11 GMT 2025 , Edited by admin on Mon Mar 31 22:52:11 GMT 2025
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