disodium 5-acetamido-2-[2-(4-isothiocyanato-2-sulfonatophenyl)ethenyl]benzene-1-sulfonate

• ChemBase ID: 136811
• Molecular Formular: C17H12N2Na2O7S3
• Molecular Mass: 498.46092
• Monoisotopic Mass: 497.9602023
• SMILES: CC(=O)Nc1ccc(c(c1)S(=O)(=O)[O-])/C=C/c1ccc(cc1S(=O)(=O)[O-])N=C=S.[Na+].[Na+]
• Canonical SMILES: S=C=Nc1ccc(c(c1)S(=O)(=O)[O-])/C=C/c1ccc(cc1S(=O)(=O)[O-])NC(=O)C.[Na+].[Na+]
• InChI: InChI=1S/C17H14N2O7S3.2Na/c1-11(20)19-15-7-5-13(17(9-15)29(24,25)26)3-2-12-4-6-14(18-10-27)8-16(12)28(21,22)23;;/h2-9H,1H3,(H,19,20)(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2
• InChIKey: NPAWAMRXPHRVQY-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 5-acetamido-2-[2-(4-isothiocyanato-2-sulfonatophenyl)ethenyl]benzene-1-sulfonate
• IUPAC Traditional name: disodium 5-acetamido-2-[2-(4-isothiocyanato-2-sulfonatophenyl)ethenyl]benzenesulfonate
• Synonyms: SITS; Disodium 4-acetamido-4′-isothiocyanato-stilben-2,2′-disulfonate; 4-Acetamido-4′-isothiocyanato-2,2′-stilbenedisulfonic acid disodium salt hydrate; 二钠4-乙酰氨基-4′-异硫氰酸芪-2,2′-二磺酸; 4-乙酰氨基-4′-异硫氰酸芪-2,2′-磺酸二钠盐 二钠盐 水合物

Database IDs

• CAS Number: 51023-76-8
• EC Number: 256-919-4
• MDL Number: MFCD00007485
• Beilstein Number: 9177451
• PubChem SID: 24890434; 162231079
• PubChem CID: 5702774

CALCULATED PROPERTIES

• Acid pKa: -2.9663773
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.8179762
• LogD (pH = 7.4): -1.8183569
• Log P: 0.7800112
• Molar Refractivity: 112.4403 cm^3
• Polarizability: 43.16943 Å^3
• Polar Surface Area: 155.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38-42
• Safety Statements: 22-26-36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H319-H334-H335
• GHS Precautionary statements: P261-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥80%; ≥90% (HPLC); 80%
• Grade: for fluorescence; technical grade
• Empirical Formula (Hill Notation): C17H12N2Na2O7S3 · xH2O

DETAILS

Sigma Aldrich - A0554

Other Notes
Predominantly trans-isomer
Application
Fluorescent marker for membranes; inhibits anion permeability of membranes. Also inactivates Na,K-ATPase, by covalent modification of a specific Lys residue.1

Sigma Aldrich - 00309

Other Notes
Non-penetrating fluorescent marker of membranes 1; Fluorochrome in immunofluorescence 2; Specific inhibitor of anion permeability in membranes 3