chrysobactin (CHEBI:61345)

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CHEBI:61345 - chrysobactin

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ChEBI ID	CHEBI:61345
ChEBI Name	chrysobactin
Stars
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.
Last Modified	3 February 2015
Submitter	hdrabkin
Downloads	Molfile

Formula	C16H23N3O7
Net Charge	0
Average Mass	369.374
Monoisotopic Mass	369.15360
SMILES	NCCCC[C@@H](NC(=O)c1cccc(O)c1O)C(=O)N[C@@H](CO)C(=O)O
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

Species of Metabolite	Component	Source	Comments
Dickeya chrysanthemi (ncbitaxon:556)	-	PubMed (18803373)

Roles Classification

Chemical Roles:	siderophore Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron. Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	siderophore Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

ChEBI Ontology

Outgoing Relation(s)
	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 Xrefs	Databases
CPD-12582	MetaCyc

Registry Numbers	Sources
CAS:120124-51-8	ChemIDplus

Citations