pyochelin (PAMDB110360)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110360
Identification
Name: pyochelin
Description:A 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, it is it 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.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • salicylic acid
  • o-hydroxybenzoic acid
  • 2-hydroxybenzoic acid
  • SA
  • 2-HBA

  •   2-hydroxybenzoate
  • o-hydroxybenzoate'
  • WIDTH
  • 500);" onmouseout="return nd();">salicylate and two molecules of L-cysteine. The structure of pyochelin was established as 2-(2-o-hydroxyphenyl-2-thiazolin-4-yl)-3-methylthiazolidine-4-carboxylic acid [Cox81]. The compounds exists in two stereoisomers ( pyochelin and enantio-pyochelin)
  • which are produced by different organisms [Youard07
  • Hoegy09].
Chemical Formula: C14H15N2O3S2
Average Molecular Weight: 324.0602337703
Monoisotopic Molecular Weight: 324.0602337703
InChI Key: NYBZAGXTZXPYND-GBIKHYSHSA-M
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)/p-1/t9-,10+,13-/m1/s1
CAS number: Not Available
IUPAC Name:(4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid
Traditional IUPAC Name: Not Available
SMILES:CN1(C(C([O-])=O)CS[CH]1[CH]3(CSC(C2(C(O)=CC=CC=2))=N3))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Imidothiolactone
  • Benzenoid
  • Thiazolidine
  • Meta-thiazoline
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
  • a thiazoline siderophore (CPD-9992)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
3D Conformer46173412 PubChem
Molecular Weight323.405 g/molPubChem
XLogP3-AA0.5 PubChem
Hydrogen Bond Donor Count1 PubChem
Hydrogen Bond Acceptor Count7 PubChem
Rotatable Bond Count1 PubChem
Exact Mass323.052 g/molPubChem
Monoisotopic Mass323.052 g/molPubChem
Topological Polar Surface Area123 A^2PubChem
Heavy Atom Count21 PubChem
Formal Charge-1 PubChem
Complexity565 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count3 PubChem
Undefined Atom Stereocenter Count0 PubChem
Defined Bond Stereocenter Count1 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
salicylate + L-Cysteine + S-Adenosylmethionine + NADPH → pyochelin + S-Adenosylhomocysteine + NADP+ + Water
Pathways:
Spectra
Spectra: Not Available
References
References:
  • Cox CD, Rinehart KL, Moore ML, Cook JC (1981)Pyochelin: novel structure of an iron-chelating growth promoter for Pseudomonas aeruginosa. Proceedings of the National Academy of Sciences of the United States of America 78, Pubmed: 6794030
  • Schlegel K, Taraz K, Budzikiewicz H (2004)The stereoisomers of pyochelin, a siderophore of Pseudomonas aeruginosa. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 17, Pubmed: 15259361
  • Youard ZA, Wenner N, Reimmann C (2011)Iron acquisition with the natural siderophore enantiomers pyochelin and enantio-pyochelin in Pseudomonas species. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 24, Pubmed: 21188474
  • Hoegy F, Lee X, Noel S, Rognan D, Mislin GL, Reimmann C, Schalk IJ (2009)Stereospecificity of the siderophore pyochelin outer membrane transporters in fluorescent pseudomonads. The Journal of biological chemistry 284, Pubmed: 19297329
  • Crosa JH, Walsh CT (2002)Genetics and assembly line enzymology of siderophore biosynthesis in bacteria. Microbiology and molecular biology reviews : MMBR 66, Pubmed: 12040125
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI29669
KEGGC12037
MetaboLightsMTBLC29669
PubChem46173412