CHEBI:61345 - chrysobactin

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ChEBI Name chrysobactin
ChEBI ID CHEBI:61345
Definition A catechol-type siderophore with a structure of D-lysyl-L-serine substituted on N2 of the lysyl residue by a 2,3-dihydroxybenzoyl group. It is produced by the Gram-negative bacillus Dickeya dadantii (previously known as Erwinia chrysanthem). Only the catecholate hydroxyl groups participate in metal coordination, so chrysobactin cannot provide full 1:1 coordination of Fe(III); at neutral pH and concentrations of about 0.1 mM, ferric chrysobactin exists as a mixture of bis and tris complexes.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Harold Drabkin
Supplier Information
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Formula C16H23N3O7
Net Charge 0
Average Mass 369.36970
Monoisotopic Mass 369.15360
InChI InChI=1S/C16H23N3O7/c17-7-2-1-5-10(15(24)19-11(8-20)16(25)26)18-14(23)9-4-3-6-12(21)13(9)22/h3-4,6,10-11,20-22H,1-2,5,7-8,17H2,(H,18,23)(H,19,24)(H,25,26)/t10-,11+/m1/s1
InChIKey NNTXFOAPABMVEG-MNOVXSKESA-N
SMILES NCCCC[C@@H](NC(=O)c1cccc(O)c1O)C(=O)N[C@@H](CO)C(O)=O
Metabolite of Species Details
Dickeya chrysanthemi (NCBI:txid556) 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.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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 chrysobactin (CHEBI:61345) has role bacterial metabolite (CHEBI:76969)
chrysobactin (CHEBI:61345) has role siderophore (CHEBI:26672)
chrysobactin (CHEBI:61345) is a catechols (CHEBI:33566)
chrysobactin (CHEBI:61345) is a dipeptide (CHEBI:46761)
chrysobactin (CHEBI:61345) is a monocarboxylic acid (CHEBI:25384)
chrysobactin (CHEBI:61345) is a primary alcohol (CHEBI:15734)
chrysobactin (CHEBI:61345) is a primary amino compound (CHEBI:50994)
IUPAC Name
N2-(2,3-dihydroxybenzoyl)-D-lysyl-L-serine
Synonym Source
2-(2,3-dihydroxybenzoyl)-D-lysyl-L-serine SUBMITTER
Manual Xref Database
CPD-12582 MetaCyc
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Registry Number Type Source
120124-51-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12231882 PubMed citation Europe PMC
1392469 PubMed citation Europe PMC
1787788 PubMed citation Europe PMC
18803373 PubMed citation Europe PMC
8837459 PubMed citation Europe PMC
PMC207143 PubMed Central citation Europe PMC
Last Modified
03 February 2015