Record Information
Version2.0
Creation Date2012-07-30 14:54:58 -0600
Update Date2015-06-03 17:20:54 -0600
Secondary Accession Numbers
  • ECMDB21212
Identification
Name:Enterochelin
DescriptionEnterobactin (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.
Structure
Thumb
Synonyms:
  • (3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)
  • Enterobactin
  • Enterochelin
  • H6ent
  • N,N',N''-[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)
  • Tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester
  • Tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester
Chemical Formula:C30H27N3O15
Weight:Average: 669.5465
Monoisotopic: 669.144217209
InChI Key:SERBHKJMVBATSJ-BZSNNMDCSA-N
InChI: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
CAS number:28384-96-5
IUPAC Name:N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide
Traditional IUPAC Name:enterobactin
SMILES:OC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1O
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP1.62ALOGPS
logP2.26ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area287.58 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity157.87 m³·mol⁻¹ChemAxon
Polarizability61.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Enterobactin BiosynthesisPW002048 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-4900010000-7da05f633e017bd648e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0420219000-bc050d4af6ea8c7f55a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910212000-3e3394d49c959159af26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-0910100000-8fa98785d303756d2b05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0940516000-dbc2d7c20e7c08be2c51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0890510000-877c1902065a851d92e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2930000000-55fd6f6a09160ff20c53View in MoNA
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28855
HMDB IDHMDB0032199
Pubchem Compound ID34231
Kegg IDC05821
ChemSpider ID31543
WikipediaEnterochelin
BioCyc IDENTEROBACTIN
EcoCyc IDENTEROBACTIN
Ligand ExpoEB4

Enzymes

General function:
Involved in ligase activity
Specific function:
Activates the carboxylate group of L-serine via ATP- dependent PPi exchange reactions to the aminoacyladenylate, preparing that molecule for the final stages of enterobactin synthesis. Holo-entF acts as the catalyst for the formation of the three amide and three ester bonds present in the cyclic (2,3- dihydroxybenzoyl)serine trimer enterobactin, using seryladenylate and acyl-holo-entB (acylated with 2,3-dihydroxybenzoate by entE)
Gene Name:
entF
Uniprot ID:
P11454
Molecular weight:
141990
Reactions
ATP + L-serine = diphosphate + L-serine-adenylate.
General function:
Involved in iron ion binding
Specific function:
Upon internalization, ferric enterobactin is processed via an exquisitely specific pathway that is dependent on FES activity, making iron available for metabolic use
Gene Name:
fes
Uniprot ID:
P13039
Molecular weight:
42569
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the transfer of the 4'-phosphopantetheine moiety from coenzyme A to apo-domains of both entB (an ArCP domain) and entF (a PCP domain). Plays an essential role in the assembly of the enterobactin
Gene Name:
entD
Uniprot ID:
P19925
Molecular weight:
23604
Reactions
CoA + apo-EntB/F = adenosine 3',5'-bisphosphate + holo-EntB/F.

Transporters

General function:
Involved in siderophore transport
Specific function:
Exports the siderophore enterobactin out of the cell
Gene Name:
entS
Uniprot ID:
P24077
Molecular weight:
43281
General function:
Involved in transporter activity
Specific function:
Required for proper expression of outer membrane protein genes such as ompF, nmpC, protein 2, hemolysin, colicin V, or colicin E1. May be specialized for signal sequence independent, extracellular secretion in Gram-negative bacteria
Gene Name:
tolC
Uniprot ID:
P02930
Molecular weight:
53740