disodium 2-hydroxy-5-[4,5,6,7-tetrabromo-1-(4-hydroxy-3-sulfonatophenyl)-3-oxo-1,3-dihydro-2-benzofuran-1-yl]benzene-1-sulfonate hydrate

• ChemBase ID: 130845
• Molecular Formular: C20H10Br4Na2O11S2
• Molecular Mass: 856.01234
• Monoisotopic Mass: 851.6193397
• SMILES: c1cc(c(cc1C1(c2c(c(c(c(c2Br)Br)Br)Br)C(=O)O1)c1ccc(c(c1)S(=O)(=O)[O-])O)S(=O)(=O)[O-])O.O.[Na+].[Na+]
• Canonical SMILES: Brc1c(Br)c(Br)c2c(c1Br)C(=O)OC2(c1ccc(c(c1)S(=O)(=O)[O-])O)c1ccc(c(c1)S(=O)(=O)[O-])O.O.[Na+].[Na+]
• InChI: InChI=1S/C20H10Br4O10S2.2Na.H2O/c21-15-13-14(16(22)18(24)17(15)23)20(34-19(13)27,7-1-3-9(25)11(5-7)35(28,29)30)8-2-4-10(26)12(6-8)36(31,32)33;;;/h1-6,25-26H,(H,28,29,30)(H,31,32,33);;;1H2/q;2*+1;/p-2
• InChIKey: CDTNUNQQEUGDSD-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 2-hydroxy-5-[4,5,6,7-tetrabromo-1-(4-hydroxy-3-sulfonatophenyl)-3-oxo-1,3-dihydro-2-benzofuran-1-yl]benzene-1-sulfonate hydrate
• IUPAC Traditional name: disodium bromosulfophthalein(2-) hydrate
• Synonyms: BSP; Bromsulfalein sodium disodium salt hydrate; Sulfobromophthalein disodium salt hydrate

Database IDs

• CAS Number: 123359-42-2
• EC Number: 200-761-0
• MDL Number: MFCD00150017
• PubChem SID: 162225123; 24850200; 24899433
• PubChem CID: 16211367

CALCULATED PROPERTIES

• Acid pKa: -3.4356573
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 2.3373277
• LogD (pH = 7.4): 2.3372722
• Log P: 7.0901256
• Molar Refractivity: 140.5301 cm^3
• Polarizability: 55.882214 Å^3
• Polar Surface Area: 181.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Absorption Wavelength: λmax 366 nm; λmax 577 nm (2nd)

Safety Information

• RTECS: SM8395000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C20H8Br4Na2O10S2 · xH2O

DETAILS

Sigma Aldrich - S0252

Biochem/physiol Actions
Sulfobromophthalein (BSP) is a high affinity substrate for organic anion transporting polypeptides (OATPs)1,2 and has been used as a substrate for multidrug resistance associated protein 2 (Mrp2). BSP is transported into hepatocytes by OATPs and, after conjugation to glutathione, is excreted into bile by Mrp2.3 It was found to inhibit the aldo-keto reductase ARK1C20.4

Sigma Aldrich - 167207

Packaging
1 g in glass bottle