pyochelin I (CHEBI:67183)

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CHEBI:67183 - pyochelin I

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ChEBI ID	CHEBI:67183
ChEBI Name	pyochelin I
Stars
Definition	A pyochelin that has R-stereochemistry at the thioaminal centre; the diastereoisomer with S-stereochemistry at this centre is pyochelin II. Pseudomonas aeruginosa produces a mixture of pyochelin I (major) and pyochelin II (minor) via condensation of salicylic acid and two molecules of cysteine. The enantiomeric compounds, enant-pyochelin I and II, are produced by Pseudomonas fluorescens.
Last Modified	21 August 2012
Submitter	Gareth Owen
Downloads	Molfile

Formula	C14H16N2O3S2
Net Charge	0
Average Mass	324.427
Monoisotopic Mass	324.06023
SMILES	[H][C@]1([C@@]2([H])SC[C@@H](C(=O)O)N2C)CSC(c2ccccc2O)=N1
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-GBIKHYSHSA-N

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 acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). 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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

ChEBI Ontology

Outgoing Relation(s)
	pyochelin I (CHEBI:67183) is a pyochelin (CHEBI:29669)

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

Synonym	Source
(4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid	ChEBI

Manual Xrefs	Databases
CPD-9992	MetaCyc

Registry Numbers	Sources
Reaxys:7255526	Reaxys

Citations