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

• ChemBase ID: 155284
• Molecular Formular: C22H33N5O7S3
• Molecular Mass: 575.72172
• Monoisotopic Mass: 575.15421142
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCSSCCC(=O)NCCNC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: O=C(CCSSCCC(=O)ON1C(=O)CCC1=O)NCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C22H33N5O7S3/c28-16(4-2-1-3-15-21-14(13-35-15)25-22(33)26-21)23-9-10-24-17(29)7-11-36-37-12-8-20(32)34-27-18(30)5-6-19(27)31/h14-15,21H,1-13H2,(H,23,28)(H,24,29)(H2,25,26,33)/t14-,15-,21-/m0/s1
• InChIKey: LWPHUVGDBNUVHA-GXZWQRSESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-({2-[(2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}ethyl)carbamoyl]ethyl}disulfanyl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-({2-[(2-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}ethyl)carbamoyl]ethyl}disulfanyl)propanoate
• Synonyms: (2-[Biotinamido]ethylamido)-3,3′-dithiodipropionic acid N-hydroxysuccinimide ester; Biotin disulfide N-hydroxysuccinimide ester

Database IDs

• CAS Number: 142439-92-7
• MDL Number: MFCD00466919
• PubChem SID: 162249422; 24891785
• PubChem CID: 71312116

CALCULATED PROPERTIES

• Acid pKa: 13.485502
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.9204505
• LogD (pH = 7.4): -0.92045003
• Log P: -0.92044973
• Molar Refractivity: 140.7331 cm^3
• Polarizability: 55.338226 Å^3
• Polar Surface Area: 163.01 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble50 mg/mL
• Apperance: powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360D
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (TLC)
• Empirical Formula (Hill Notation): C22H33N5O7S3

DETAILS

Sigma Aldrich - B4531

Application
Biotinylation reagent incorporating a spacer with a cleavable disulfide linkage. Typically coupled to primary amine in the pH range 6.5-8.5. Cleavage of disulfide requires reducing agent allowing mild recovery of biotinylated compound.