CHEBI:29707 - yersiniabactin

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ChEBI Name yersiniabactin
ChEBI ID CHEBI:29707
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H27N3O4S3
Net Charge 0
Average Mass 481.640
Monoisotopic Mass 481.11637
InChI InChI=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
InChIKey JHYVWAMMAMCUIR-VQNLDRKJSA-N
SMILES C=1C=CC(=C(C1)C2=N[C@](CS2)(C3SC[C@](N3)([C@H](C(C4=N[C@](CS4)(C(O)=O)C)(C)C)O)[H])[H])O
Metabolite of Species Details
Yersinia enterocolitica (NCBI:txid630) See: DOI
Yersinia pestis (NCBI:txid632) See: PubMed
Roles Classification
Chemical Role(s): siderophore
Any of low-molecular-mass iron(3)-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 (Bronsted base).
(via oxoacid )
Biological Role(s): siderophore
Any of low-molecular-mass iron(3)-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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
Ybt ChEBI
yersiniabactin KEGG COMPOUND
Manual Xrefs Databases
C00029246 KNApSAcK
C12038 KEGG COMPOUND
CPD-9991 MetaCyc
O34 PDBeChem
Yersiniabactin Wikipedia
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Citations Waiting for Citations Types Sources
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Last Modified
21 April 2020