2,5-dioxopyrrolidin-1-yl (2R)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-(pyridin-2-yldisulfanyl)propanoate

• ChemBase ID: 162125
• Molecular Formular: C22H27N5O6S3
• Molecular Mass: 553.67468
• Monoisotopic Mass: 553.11234661
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)N[C@H](C(=O)ON1C(=O)CCC1=O)CSSc1ccccn1
• Canonical SMILES: O=C(N[C@H](C(=O)ON1C(=O)CCC1=O)CSSc1ccccn1)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C22H27N5O6S3/c28-16(6-2-1-5-15-20-13(11-34-15)25-22(32)26-20)24-14(12-35-36-17-7-3-4-10-23-17)21(31)33-27-18(29)8-9-19(27)30/h3-4,7,10,13-15,20H,1-2,5-6,8-9,11-12H2,(H,24,28)(H2,25,26,32)/t13-,14-,15-,20-/m0/s1
• InChIKey: LSXCUZMTPAIGMX-KZDUYQQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl (2R)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-(pyridin-2-yldisulfanyl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl (2R)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-3-(pyridin-2-yldisulfanyl)propanoate
• Synonyms: Biotinyl Pyridinyldithio N-Hydroxysuccinimide Alanine Ester

Database IDs

• CAS Number: 1356933-91-9
• PubChem SID: 162256260
• PubChem CID: 71314012

CALCULATED PROPERTIES

• Acid pKa: 11.7759
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.7079726
• LogD (pH = 7.4): 0.70839506
• Log P: 0.7084169
• Molar Refractivity: 134.2274 cm^3
• Polarizability: 53.550854 Å^3
• Polar Surface Area: 146.8 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B397300

An antimicrobial bisulfide prodrug.

REFERENCES

• Hausch, F., et al.: Bioconjug. Chem., 8, 885 (1981)
• Seelig, B., et al.: Chem. Biol., 6, 167 (1981)
• Ponpipom, et al.: J. Med. Chem., 24, 1388 (1981)