(2S)-2-{[(2R,3R,4R,5S,6R)-3-[(2R)-2-amino-3-sulfanylpropanamido]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanedioic acid

• ChemBase ID: 126012
• Molecular Formular: C13H22N2O10S
• Molecular Mass: 398.38618
• Monoisotopic Mass: 398.09951591
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H](CC(=O)O)C(=O)O)NC(=O)[C@H](CS)N)O)O)O
• Canonical SMILES: SC[C@@H](C(=O)N[C@H]1[C@H](O[C@@H]([C@H]([C@@H]1O)O)CO)O[C@H](C(=O)O)CC(=O)O)N
• InChI: InChI=1S/C13H22N2O10S/c14-4(3-26)11(21)15-8-10(20)9(19)6(2-16)25-13(8)24-5(12(22)23)1-7(17)18/h4-6,8-10,13,16,19-20,26H,1-3,14H2,(H,15,21)(H,17,18)(H,22,23)/t4-,5-,6+,8+,9+,10+,13-/m0/s1
• InChIKey: UHNHELGKNQMNGF-AOQKXWSCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2R,3R,4R,5S,6R)-3-[(2R)-2-amino-3-sulfanylpropanamido]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanedioic acid
• IUPAC Traditional name: bacillithiol
• Synonyms: Bacillithiol

Database IDs

• PubChem SID: 162220355
• PubChem CID: 42614123
• CHEBI ID: 61338
• Chemspider ID: 24604693
• Wikipedia Title: Bacillithiol

CALCULATED PROPERTIES

• Acid pKa: 3.1307375
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -6.543762
• LogD (pH = 7.4): -8.397308
• Log P: -5.846515
• Molar Refractivity: 83.9697 cm^3
• Polarizability: 34.50918 Å^3
• Polar Surface Area: 208.87 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Density: 1.629 g/mL