pyochelin I (PAMDB100050)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB100050
Identification
Name: pyochelin I
Description: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
Structure
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (4'R,2''R,4''R)-2'-(2-
Chemical Formula: C14H16N2O3S2
Average Molecular Weight: 324.418
Monoisotopic Molecular Weight: 324.06
InChI Key: NYBZAGXTZXPYND-GBIKHYSHSA-N
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/h2-5,9-10,13,15H,6-7H2,1H3,(H,18,19)/b12-8-/t9-,10+,13-/m1/s1
CAS number: Not Available
IUPAC Name:(2R,4R)-3-methyl-2-[(2Z,4R)-2-(6-oxocyclohexa-2,4-dien-1-ylidene)-1,3-thiazolidin-4-yl]-1,3-thiazolidine-4-carboxylic acid
Traditional IUPAC Name: Not Available
SMILES:[H][C@@]1(CSC(=N1)c1ccccc1O)[C@@]1([H])SC[C@H](N1C)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent L-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Imidothiolactone
  • Thiazolidine
  • Meta-thiazoline
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Hemithioaminal
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Dialkylthioether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
  • pyochelin (CHEBI:67183)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass324.4229ChemAxon
logP1.0856ChemAxon
H-bond acceptors5ChemAxon
H-bond donors2ChemAxon
Rotatable bonds3ChemAxon
PSA123.7300ChemAxon
RO5 violations0ChemAxon
RO3 violations3ChemAxon
Refractivity93.6278ChemAxon
Atoms37ChemAxon
Rings3ChemAxon
Heavy atoms21ChemAxon
Hydrogen atoms16ChemAxon
Heteroatoms7ChemAxon
N/O atoms5ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms0ChemAxon
Chiral centers3ChemAxon
R/S chiral centers3ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers0ChemAxon
Stereo double bonds0ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds0ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Schlegel K, Taraz K, Budzikiewicz H. The stereoisomers of pyochelin, a siderophore of Pseudomonas aeruginosa. Biometals. 2004 Aug;17(4):409-14. Pubmed: 15259361
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    MetaCycCPD-9992