CHEBI:28855 - enterobactin

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ChEBI Name enterobactin
ChEBI ID CHEBI:28855
Definition A macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:23923, CHEBI:4799
Supplier Information
Download Molfile XML SDF
Formula C30H27N3O15
Net Charge 0
Average Mass 669.54660
Monoisotopic Mass 669.14422
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
InChIKey SERBHKJMVBATSJ-BZSNNMDCSA-N
SMILES Oc1cccc(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)c2cccc(O)c2O)NC(=O)c2cccc(O)c2O)c1O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Chemical Role(s): siderophore
Any of low-molecular-mass iron(3)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
siderophore
Any of low-molecular-mass iron(3)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide) ChemIDplus
Enterobactin KEGG COMPOUND
Enterochelin KEGG COMPOUND
H6ent ChEBI
Tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester KEGG COMPOUND
Tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester KEGG COMPOUND
Manual Xrefs Databases
C00000735 KNApSAcK
C05821 KEGG COMPOUND
EB4 PDBeChem
View more database links
Registry Numbers Types Sources
1420020 Beilstein Registry Number Beilstein
28384-96-5 CAS Registry Number KEGG COMPOUND
28384-96-5 CAS Registry Number ChemIDplus
781435 Gmelin Registry Number Gmelin
Last Modified
02 December 2019