pyochelin (CHEBI:29669)

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ChEBI Name	pyochelin

ChEBI ID	CHEBI:29669

Definition	A member of the class of thiazolidines that is (4R)-3-methyl-1,3-thiazolidine-4-carboxylic acid which is substituted at position 2 by a (4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl group. A siderophore that is produced by Pseudomonas aeruginosa (via condensation of salicylic acid and two molecules of cysteine) as a mixture of two easily interconvertible diastereoisomers, pyochelin I (major) and pyochelin II (minor). The enantiomeric compounds, enant-pyochelin, are produced by Pseudomonas fluorescens.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C14H16N2O3S2

Net Charge

Average Mass

324.41800

Monoisotopic Mass

324.06023

InChI

InChI=1S/C14H16N2O3S2/c1-16-10(14(18)19)7-21-13(16)9-6-20-12(15-9)8-4-2-3-5-11(8)17/h2-5,9-10,13,17H,6-7H2,1H3,(H,18,19)/t9-,10+,13?/m1/s1

InChIKey

NYBZAGXTZXPYND-GDVCOKDOSA-N

SMILES

[H][C@@]1(CSC(=N1)c1ccccc1O)C1SC[C@H](N1C)C(O)=O

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 )

Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. siderophore Any of low-molecular-mass iron(3)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.

ChEBI Ontology
Outgoing	pyochelin (CHEBI:29669) has role metabolite (CHEBI:25212) pyochelin (CHEBI:29669) has role siderophore (CHEBI:26672) pyochelin (CHEBI:29669) is a monocarboxylic acid (CHEBI:25384) pyochelin (CHEBI:29669) is a phenols (CHEBI:33853) pyochelin (CHEBI:29669) is a thiazolidines (CHEBI:35622)

Incoming	pyochelin I (CHEBI:67183) is a pyochelin (CHEBI:29669) pyochelin II (CHEBI:67185) is a pyochelin (CHEBI:29669)

IUPAC Name

(4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid

Synonym	Source
Pyochelin	KEGG COMPOUND

Last Modified

20 April 2020