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CHEBI:29707 - yersiniabactin

ChEBI IDCHEBI:29707
ChEBI Nameyersiniabactin
Stars
DefinitionA member of the class of thiazolidines that is (4S)-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid which is substituted at position 2 by a (1S)-1-hydroxy-1-{(4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazolidin-4-yl}-2-methylpropan-2-yl group. A siderophore found in the gram-negative bacterium species, Yersinia enterocolitica and Yersinia pestis.
Last Modified21 April 2020
DownloadsMolfile
FormulaC21H27N3O4S3
Net Charge0
Average Mass481.665
Monoisotopic Mass481.11637
SMILES[H][C@]1(C2N[C@]([H])([C@@H](O)C(C)(C)C3=N[C@@](C)(C(=O)O)CS3)CS2)CSC(c2ccccc2O)=N1
InChIInChI=1S/C21H27N3O4S3/c1-20(2,18-24-21(3,10-31-18)19(27)28)15(26)12-8-30-17(22-12)13-9-29-16(23-13)11-6-4-5-7-14(11)25/h4-7,12-13,15,17,22,25-26H,8-10H2,1-3H3,(H,27,28)/t12-,13+,15+,17?,21+/m0/s1
InChIKeyJHYVWAMMAMCUIR-VQNLDRKJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Yersinia enterocolitica (ncbitaxon:630) - DOI (/10.1016/S0040-4020(01)00012-6)
Yersinia pestis (ncbitaxon:632) - PubMed (22045585)
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:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
ChEBI Ontology
Outgoing Relation(s)
yersiniabactin (CHEBI:29707) has role bacterial metabolite (CHEBI:76969)
yersiniabactin (CHEBI:29707) has role siderophore (CHEBI:26672)
yersiniabactin (CHEBI:29707) is a monocarboxylic acid (CHEBI:25384)
yersiniabactin (CHEBI:29707) is a phenols (CHEBI:33853)
yersiniabactin (CHEBI:29707) is a secondary alcohol (CHEBI:35681)
yersiniabactin (CHEBI:29707) is a thiazolidines (CHEBI:35622)
yersiniabactin (CHEBI:29707) is conjugate acid of yersiniabactin(1−) (CHEBI:149525)
Incoming Relation(s)
yersiniabactin(1−) (CHEBI:149525) is conjugate base of yersiniabactin (CHEBI:29707)
IUPAC Name 
(4S)-2-[(1S)-1-hydroxy-1-{(4R)-2-[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazolidin-4-yl}-2-methylpropan-2-yl]-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid
Synonyms  Source
yersiniabactinKEGG COMPOUND
YbtChEBI
Manual XrefsDatabases
C12038KEGG COMPOUND
CPD-9991MetaCyc
YersiniabactinWikipedia
O34PDBeChem
C00029246KNApSAcK
Citations