Basic information
- CAS
152166-40-0- Standard SMILES
CC(C)(C1=N[C@@](C)(C(=O)O)CS1)[C@H](O)[C@@H]1CSC([C@H]2CSC(c3ccccc3O)=N2)N1- InChIKey
JHYVWAMMAMCUIR-VQNLDRKJSA-N- Molecular formula
- C21H27N3O4S3
- Average molar mass
- 481.7 g/mol
- Monoisotopic mass
- 481.11636987
Overview
Yersiniabactin is 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. It has a role as a siderophore and a bacterial metabolite. It is a monocarboxylic acid, a member of phenols, a member of thiazolidines and a secondary alcohol. It is a conjugate acid of a yersiniabactin(1-).
Names & identifiers
- Preferred name
- Yersiniabactin
- IUPAC
- (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-5H-1,3-thiazole-4-carboxylic acid
- English name
- 4-Thiazolecarboxylic acid, 2-[(2S)-2-[(4R)-2-[(4R)-4,5-dihydro-2-(2-hydroxyphenyl)-4-thiazolyl]-4-thiazolidinyl]-2-hydroxy-1,1-dimethylethyl]-4,5-dihydro-4-methyl-, (4S)-
- Molecular formula
- C21H27N3O4S3
- Molecular weight
- 481.65
Names & synonyms
Yersiniabactin152166-40-0CHEBI:29707DTXSID501029725(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-5H-1,3-thiazole-4-carboxylic acid(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-5H-1,3-thiazole-4-carboxylic acid(4S)-2-((2S)-2-hydroxy-1,1-dimethyl-2-((4R)-2-((2E,4R)-2-(6-oxocyclohexa-2,4-dien-1-ylidene)thiazolidin-4-yl)thiazolidin-4-yl)ethyl)-4-methyl-5H-thiazole-4-carboxylic acid(4S)-2-[(2S)-2-hydroxy-1,1-dimethyl-2-[(4R)-2-[(2E,4R)-2-(6-oxocyclohexa-2,4-dien-1-ylidene)thiazolidin-4-yl]thiazolidin-4-yl]ethyl]-4-methyl-5H-thiazole-4-carboxylic acidRefChem:195630DTXCID601514941CHEMBL1221692C12038
Show more names
4-Thiazolecarboxylic acid, 2-[(2S)-2-[(4R)-2-[(4R)-4,5-dihydro-2-(2-hydroxyphenyl)-4-thiazolyl]-4-thiazolidinyl]-2-hydroxy-1,1-dimethylethyl]-4,5-dihydro-4-methyl-, (4S)-
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 190 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 777
Physicochemical properties
- Boiling point
- 718.3 · 718.3±70.0 °C(Predicted)
- Density
- 1.54 · 1.54±0.1 g/cm3(Predicted)
- pka
- 1.1 · 1.10±0.40(Predicted)
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationLow-molecular-weight compounds produced by microorganisms that aid in the transport and sequestration of ferric iron. (The Encyclopedia of Molecular Biology, 1994)
Suppliers1 total
湖北扬信医药科技有限公司0714-3999001 19171453112 · [email protected]
Additional notes
DefinitionChEBI: Yersiniabactin is 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. It has a role as a siderophore and a bacterial metabolite. It is a member of phenols, a member of thiazolidines, a monocarboxylic acid and a secondary alcohol. It is a conjugate acid of a yersiniabactin(1-).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…