ethyl 2-[5-(methylsulfanyl)thiophene-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

• ChemBase ID: 154964
• Molecular Formular: C18H19NO3S2
• Molecular Mass: 361.47836
• Monoisotopic Mass: 361.08063547
• SMILES: CCOC(=O)C1Cc2ccccc2CN1C(=O)c1ccc(s1)SC
• Canonical SMILES: CCOC(=O)C1Cc2ccccc2CN1C(=O)c1ccc(s1)SC
• InChI: InChI=1S/C18H19NO3S2/c1-3-22-18(21)14-10-12-6-4-5-7-13(12)11-19(14)17(20)15-8-9-16(23-2)24-15/h4-9,14H,3,10-11H2,1-2H3
• InChIKey: UIEBLUZPSFAFOC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-[5-(methylsulfanyl)thiophene-2-carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• IUPAC Traditional name: ethyl 2-[5-(methylsulfanyl)thiophene-2-carbonyl]-3,4-dihydro-1H-isoquinoline-3-carboxylate
• Synonyms: 1,2,3,4-Tetrahydro-2-[[5-(methylthio)-2-thienyl]carbonyl]-3-isoquinolinecarboxylic acid ethyl ester; SR8278

Database IDs

• CAS Number: 1254944-66-5
• MDL Number: MFCD18782736
• PubChem SID: 162249102
• PubChem CID: 53393127

CALCULATED PROPERTIES

• H Donor: 0
• LogD (pH = 5.5): 3.9353359
• LogD (pH = 7.4): 3.9353359
• Log P: 3.9353359
• Molar Refractivity: 97.0083 cm^3
• Polarizability: 37.425396 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• H Acceptors: 2

PROPERTIES

Physical Property

• Solubility: DMSO: ≥30 mg/mL
• Apperance: white to tan semisolid

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C18H19NO3S2

DETAILS

Sigma Aldrich - S9576

Biochem/physiol Actions
SR8278 is a Nuclear Heme Receptor REV-ERB antagonist. REV-ERBα plays a critical role in regulation of the circadian rhythm by repressing target gene activities. Additionally, REV-ERBα has been shown to regulate metabolic processes including lipid and glucose metabolism. SR8278 blocks the ability of the synthetic agonist GSK4112 to enhance REV-ERBα-dependent repression and stimulates the expression of REV-ERBα target genes involved in gluconeogenesis.