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Enterobactin

Enterobactin structure

Enterobactin 

structure
  • CAS No:

    28384-96-5

  • Formula:

    C30H27N3O15

  • Chemical Name:

    Enterobactin

  • Synonyms:

    Benzamide,N,N′,N′′-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-;o-Pyrocatechuamide,N,N′,N′′-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris-;Benzamide,N,N′,N′′-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris[2,3-dihydroxy-,[3S-(3R*,7R*,11R*)]-;1,5,9-Trioxacyclododecane,benzamide deriv.;N,N′,N′′-[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxybenzamide];Enterobactin;Enterochelin;Enterochellin;N-(2,3-Dihydroxybenzoyl)-L-serine trimolecular cyclic ester;Cyclotris(N-2,3-dihydroxybenzoyl-L-seryl);30567-79-4;33189-71-8

Description

Enterobactin is a macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella. It has a role as a bacterial metabolite and a siderophore. It is a crown compound, a member of catechols, a polyphenol and a macrotriolide. It is a conjugate acid of an enterobactin(6-) and an enterobactin(1-).|An iron-binding cyclic trimer of 2,3-dihydroxy-N-benzoyl-L-serine. It is produced by E COLI and other enteric bacteria.

Enterobactin Basic Attributes

669.552

669.55

35C9R2N24F

DTXSID40182617

Characteristics

288

2.3

1.72±0.1 g/cm3(Predicted)

202-203°

-20°C

D25 +7.40° (ethanol)

Drug Information

Low-molecular-weight compounds produced by microorganisms that aid in the transport and sequestration of ferric iron. (The Encyclopedia of Molecular Biology, 1994) (See all compounds classified as Siderophores.)

Enterobactin

Computed Properties

Molecular Weight:669.5
XLogP3:2.3
Hydrogen Bond Donor Count:9
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:6
Exact Mass:669.14421716
Monoisotopic Mass:669.14421716
Topological Polar Surface Area:288
Heavy Atom Count:48
Complexity:1060
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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