sodium 3-[({3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}({[2-(dimethylcarbamoyl)ethyl]sulfanyl})methyl)sulfanyl]propanoate hydrate

• ChemBase ID: 154640
• Molecular Formular: C26H28ClN2NaO4S2
• Molecular Mass: 555.08429
• Monoisotopic Mass: 554.10767135
• SMILES: CN(C)C(=O)CCSC(c1cccc(c1)/C=C/c1ccc2ccc(cc2n1)Cl)SCCC(=O)[O-].O.[Na+]
• Canonical SMILES: [O-]C(=O)CCSC(c1cccc(c1)/C=C/c1ccc2c(n1)cc(cc2)Cl)SCCC(=O)N(C)C.O.[Na+]
• InChI: InChI=1S/C26H27ClN2O3S2.Na.H2O/c1-29(2)24(30)12-14-33-26(34-15-13-25(31)32)20-5-3-4-18(16-20)6-10-22-11-8-19-7-9-21(27)17-23(19)28-22;;/h3-11,16-17,26H,12-15H2,1-2H3,(H,31,32);;1H2/q;+1;/p-1
• InChIKey: MSHRPLRGSQECLY-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 3-[({3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}({[2-(dimethylcarbamoyl)ethyl]sulfanyl})methyl)sulfanyl]propanoate hydrate
• IUPAC Traditional name: sodium 3-[({3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}({[2-(dimethylcarbamoyl)ethyl]sulfanyl})methyl)sulfanyl]propanoate hydrate
• Synonyms: 5-(3-(2-(7-Chloroquinolin-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoic acid sodium salt hydrate; L-660711; MK-571 sodium salt hydrate

Database IDs

• CAS Number: 115103-85-0(anhydrous)
• MDL Number: MFCD11114392
• PubChem SID: 162248778
• PubChem CID: 71311923

CALCULATED PROPERTIES

• Acid pKa: 4.2618084
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.6334977
• LogD (pH = 7.4): 2.9135962
• Log P: 5.6703496
• Molar Refractivity: 153.3569 cm^3
• Polarizability: 56.30142 Å^3
• Polar Surface Area: 73.33 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: light yellow powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C26H26ClN2NaO3S2 · xH2O

DETAILS

Sigma Aldrich - M7571

Biochem/physiol Actions
MK 571 is a potent and selective leukotriene D4 (LTD4) antagonist and ABCC multidrug resistance protein 1(MRP1) inhibitor. The cysteinyl leukotrienes (CysLTs), LTC4, LTD4, and LTE4, mediate their actions through two distinct G-protein coupled receptors. LTD4 is the preferred ligand for the CysLT1 receptor, whereas LTC4 and LTD4 bind with approximately equal affinity to the CysLT2 receptor. MK 571 is a selective, orally active CysLT1 receptor antagonist. It blocks the binding of LTD4, but not LTC4, to human and guinea pig lung membranes with Ki values of 0.22 nM and 2.1 nM, respectively. MK 571 effectively blocks LTD4 activation of recombinant human and mouse CysLT1 receptors but is ineffective at blocking LTC4 or LTD4 activation of the recombinant human or murine CysLT2 receptors. It potentially inhibits MRP1 and has been shown to overcome acquired arsenic tolerance.