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CHEBI:67185 - pyochelin II

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:
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 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