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CHEBI:29669 - pyochelin

ChEBI IDCHEBI:29669
ChEBI Namepyochelin
Stars
DefinitionA 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.
Last Modified20 April 2020
DownloadsMolfile
FormulaC14H16N2O3S2
Net Charge0
Average Mass324.427
Monoisotopic Mass324.06023
SMILES[H][C@]1(C2SC[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-GDVCOKDOSA-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).
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 (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 Relation(s)
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
PyochelinKEGG COMPOUND
Manual XrefsDatabases
C12037KEGG COMPOUND
CPD-9992MetaCyc
C00015907KNApSAcK
Registry NumbersSources
Reaxys:8782488Reaxys
CAS:69772-54-9KEGG COMPOUND
Citations