sodium 1-{4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexanecarbonyloxy}-2,5-dioxopyrrolidine-3-sulfonate

• ChemBase ID: 130823
• Molecular Formular: C16H17N2NaO9S
• Molecular Mass: 436.36895
• Monoisotopic Mass: 436.05524542
• SMILES: C1CC(CCC1CN1C(=O)C=CC1=O)C(=O)ON1C(=O)CC(C1=O)S(=O)(=O)[O-].[Na+]
• Canonical SMILES: O=C(C1CCC(CC1)CN1C(=O)C=CC1=O)ON1C(=O)CC(C1=O)S(=O)(=O)[O-].[Na+]
• InChI: InChI=1S/C16H18N2O9S.Na/c19-12-5-6-13(20)17(12)8-9-1-3-10(4-2-9)16(23)27-18-14(21)7-11(15(18)22)28(24,25)26;/h5-6,9-11H,1-4,7-8H2,(H,24,25,26);/q;+1/p-1
• InChIKey: VUFNRPJNRFOTGK-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 1-{4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexanecarbonyloxy}-2,5-dioxopyrrolidine-3-sulfonate
• IUPAC Traditional name: sodium 1-{4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexanecarbonyloxy}-2,5-dioxopyrrolidine-3-sulfonate
• Synonyms: Sulfo-SMCC; 4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt

Database IDs

• CAS Number: 92921-24-9
• MDL Number: MFCD00054978
• PubChem SID: 162225101; 24897071
• PubChem CID: 4618794

CALCULATED PROPERTIES

• Acid pKa: -1.2492778
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): -2.7823842
• LogD (pH = 7.4): -2.7826035
• Log P: -0.406001
• Molar Refractivity: 89.6449 cm^3
• Polarizability: 36.038254 Å^3
• Polar Surface Area: 158.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; H2O: soluble2.5 mg/mL
• Apperance: white to light brown powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - M6035

Application
Water soluble, heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5). Second coupling specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Contains 9 atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.
Quality
May contain dimethylformamide.