tert-butyl 2-{[(4-chlorophenyl)methyl][(5-nitrothiophen-2-yl)methyl]amino}acetate

• ChemBase ID: 154578
• Molecular Formular: C18H21ClN2O4S
• Molecular Mass: 396.88834
• Monoisotopic Mass: 396.09105584
• SMILES: CC(C)(C)OC(=O)CN(Cc1ccc(cc1)Cl)Cc1ccc(s1)[N+](=O)[O-]
• Canonical SMILES: O=C(OC(C)(C)C)CN(Cc1ccc(s1)[N+](=O)[O-])Cc1ccc(cc1)Cl
• InChI: InChI=1S/C18H21ClN2O4S/c1-18(2,3)25-17(22)12-20(10-13-4-6-14(19)7-5-13)11-15-8-9-16(26-15)21(23)24/h4-9H,10-12H2,1-3H3
• InChIKey: WYSLOKHVFKLWOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-{[(4-chlorophenyl)methyl][(5-nitrothiophen-2-yl)methyl]amino}acetate
• IUPAC Traditional name: tert-butyl 2-{[(4-chlorophenyl)methyl][(5-nitrothiophen-2-yl)methyl]amino}acetate
• Synonyms: 1,1-Dimethylethyl N-[(4-chlorophenyl)methyl]-N-[(5-nitro-2-thienyl)methyl])glycinate; SR6452; GSK4112

Database IDs

• MDL Number: MFCD12912412
• PubChem SID: 162248716
• PubChem CID: 50905018

CALCULATED PROPERTIES

• LogD (pH = 7.4): 4.93889
• Log P: 4.939859
• Molar Refractivity: 102.0519 cm^3
• Polarizability: 39.422432 Å^3
• Polar Surface Area: 75.36 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.8689265

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: off-white to tan powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 41-43
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H318-H334
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H21ClN2O4S

DETAILS

Sigma Aldrich - G0673

Biochem/physiol Actions
GSK4112 is a rev-erbα, (orphan nuclear receptor NR1D1) agonist, the first agent able to reset the circadian clock in a phase-dependent manner. Rev-erbα impacts the precision of the circadian clock by repressing target gene activities with the help of a nuclear receptor co-repressor complex (NCoR) and HDAC3. GSK4112 competes with heme (rev-erb′s natural ligand) and enhances co-repressor complex recruitment and thus, repression of transcription. suggests that pharmacological modulation through Rev-erb may provide new routes to treat metabolic diseases, especially disorders of adipogenesis regulated by rev-erba.1