CHEBI:9973 - vibriobactin

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ChEBI Name vibriobactin
ChEBI ID CHEBI:9973
Definition A catecholate siderophore produced exclusively by Vibrio cholerae. It contains three molecules of 2,3-dihydroxybenzoate linked either directly or through L-threonine residues to the polyamine norspermidine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C35H39N5O11
Net Charge 0
Average Mass 705.71110
Monoisotopic Mass 705.26461
InChI InChI=1S/C35H39N5O11/c1-18-26(38-33(50-18)21-9-4-12-24(42)29(21)45)32(48)37-15-7-17-40(16-6-14-36-31(47)20-8-3-11-23(41)28(20)44)35(49)27-19(2)51-34(39-27)22-10-5-13-25(43)30(22)46/h3-5,8-13,18-19,26-27,41-46H,6-7,14-17H2,1-2H3,(H,36,47)(H,37,48)/t18-,19+,26+,27-/m0/s1
InChIKey LLMKLMMXMOTPRU-YOAXHERRSA-N
SMILES [H][C@]1(N=C(O[C@H]1C)c1cccc(O)c1O)C(=O)NCCCN(CCCNC(=O)c1cccc(O)c1O)C(=O)[C@@]1([H])N=C(O[C@@H]1C)c1cccc(O)c1O
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): 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 vibriobactin (CHEBI:9973) has role siderophore (CHEBI:26672)
vibriobactin (CHEBI:9973) is a 1,3-oxazoles (CHEBI:46812)
vibriobactin (CHEBI:9973) is a secondary carboxamide (CHEBI:140325)
Incoming ferric-vibriobactin (CHEBI:61375) has functional parent vibriobactin (CHEBI:9973)
IUPAC Name
(4S,5R)-N-{3-[(2,3-dihydroxybenzoyl)amino]propyl}-2-(2,3-dihydroxyphenyl)-N-[3-({[(4R,5S)-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazol-4-yl]carbonyl}amino)propyl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxamide
Synonym Source
vibriobactin UniProt
Manual Xrefs Databases
C06769 KEGG COMPOUND
CPD-2002 MetaCyc
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Registry Number Type Source
88217-23-6 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
6706943 PubMed citation Europe PMC
Last Modified
07 March 2018