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CHEBI:67185 - pyochelin II

Default Structure
ChEBI IDCHEBI:67185
ChEBI Namepyochelin II
Stars
DefinitionA pyochelin that has S-stereochemistry at the thioaminal centre; the diastereoisomer with R-stereochemistry at this centre is pyochelin I. Pseudomonas aeruginosa produces a mixture of pyochelin I (major) and pyochelin I (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 Modified21 August 2012
SubmitterGareth Owen
DownloadsMolfile
FormulaC14H16N2O3S2
Net Charge0
Average Mass324.427
Monoisotopic Mass324.06023
SMILES[H][C@]1([C@]2([H])SC[C@@H](C(=O)O)N2C)CSC(c2ccccc2O)=N1
InChIInChI=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
InChIKeyNYBZAGXTZXPYND-NRUUGDAUSA-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 II (CHEBI:67185) is a pyochelin (CHEBI:29669)
IUPAC Name 
(2S,4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid
Registry NumbersSources
Reaxys:7255524Reaxys
Citations