(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

• ChemBase ID: 130223
• Molecular Formular: C21H27N3O4S3
• Molecular Mass: 481.65178
• Monoisotopic Mass: 481.11636936
• SMILES: CC(C)([C@H](O)[C@@H]1CSC(N1)[C@H]1CSC(=N1)c1ccccc1O)C1=N[C@](C)(CS1)C(=O)O
• Canonical SMILES: O[C@@H](C(C1=N[C@@](CS1)(C)C(=O)O)(C)C)[C@@H]1CSC(N1)[C@H]1CSC(=N1)c1ccccc1O
• 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

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: yersiniabactin
• Synonyms: Yersiniabactin

Database IDs

• PubChem SID: 162224503
• PubChem CID: 5462519
• CHEMBL: 1221692
• Wikipedia Title: Yersiniabactin

CALCULATED PROPERTIES

• Acid pKa: 3.5535946
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.6184658
• LogD (pH = 7.4): 0.8790332
• Log P: 1.6368023
• Molar Refractivity: 126.3662 cm^3
• Polarizability: 49.74781 Å^3
• Polar Surface Area: 114.51 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true