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CHEBI:28855 - enterobactin

ChEBI IDCHEBI:28855
ChEBI Nameenterobactin
Stars
DefinitionA macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella.
Secondary ChEBI IDsCHEBI:4799, CHEBI:23923
Last Modified2 December 2019
DownloadsMolfile
FormulaC30H27N3O15
Net Charge0
Average Mass669.552
Monoisotopic Mass669.14422
SMILESO=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O
InChIInChI=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
InChIKeySERBHKJMVBATSJ-BZSNNMDCSA-N
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Roles Classification
Chemical Role:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
ChEBI Ontology
Outgoing Relation(s)
enterobactin (CHEBI:28855) has role bacterial metabolite (CHEBI:76969)
enterobactin (CHEBI:28855) has role siderophore (CHEBI:26672)
enterobactin (CHEBI:28855) is a catechols (CHEBI:33566)
enterobactin (CHEBI:28855) is a crown compound (CHEBI:37409)
enterobactin (CHEBI:28855) is a macrotriolide (CHEBI:145559)
enterobactin (CHEBI:28855) is a polyphenol (CHEBI:26195)
enterobactin (CHEBI:28855) is conjugate acid of enterobactin(1−) (CHEBI:77805)
enterobactin (CHEBI:28855) is conjugate acid of enterobactin(6−) (CHEBI:38150)
Incoming Relation(s)
diglucosyl-enterobactin (CHEBI:142959) has functional parent enterobactin (CHEBI:28855)
monoglucosyl-enterobactin (CHEBI:142958) has functional parent enterobactin (CHEBI:28855)
triglucosyl-enterobactin (CHEBI:142960) has functional parent enterobactin (CHEBI:28855)
enterobactin(1−) (CHEBI:77805) is conjugate base of enterobactin (CHEBI:28855)
enterobactin(6−) (CHEBI:38150) is conjugate base of enterobactin (CHEBI:28855)
IUPAC Name 
N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)
Synonyms  Source
EnterochelinKEGG COMPOUND
EnterobactinKEGG COMPOUND
Tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-esterKEGG COMPOUND
Tri-(2,3-dihydroxy-N-benzoyl-L-serine)-esterKEGG COMPOUND
(3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)ChemIDplus
H6entChEBI
Manual XrefsDatabases
C05821KEGG COMPOUND
EB4PDBeChem
C00000735KNApSAcK
Registry NumbersSources
Beilstein:1420020Beilstein
Gmelin:781435Gmelin
CAS:28384-96-5ChemIDplus
CAS:28384-96-5KEGG COMPOUND