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:	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(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.

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