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CRBN-6-5-5-VHL - CAS 2362575-45-7

Inquiry

CRBN-6-5-5-VHL is a potent and selective cereblon degrader (DC50 = 1.5 nM). It induces degradation of cereblon in MM1S cells completely.

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Molecular Formula

C51H69N7O10S

Molecular Weight

972.21

CRBN-6-5-5-VHL

- Specification
  - Purity
    
    ≥95%
    
    Solubility
    
    Soluble in DMSO
    
    Appearance
    
    Yellow Solid
    
    Storage
    
    Store at -20°C
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    (2S,4R)-1-[(2S)-2-[5-[5-[6-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]hexoxy]pentoxy]pentanoylamino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide
    
    Synonyms
    
    N-[5-({5-[(6-{[2-(2,6-Dioxo-3-piperidinyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]amino}hexyl)oxy]pentyl}oxy)pentanoyl]-3-methyl-L-valyl-(4R)-4-hydroxy-N-[4-(4-methyl-1,3-thiazol-5-yl)benzyl]-L-prolinamide; L-Prolinamide, N-[5-[[5-[[6-[[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]amino]hexyl]oxy]pentyl]oxy]-1-oxopentyl]-3-methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-, (4R)-; (2S,4R)-1-((2S)-2-(5-((5-((6-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)hexyl)oxy)pentyl)oxy)pentanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
- Properties
  - Boiling Point
    
    1152.7±65.0°C at 760 Torr
    
    Density
    
    1.265±0.06 g/cm3
    
    InChI Key
    
    LIMCHOLAKDUZDS-XARBDFOFSA-N
    
    InChI
    
    InChI=1S/C51H69N7O10S/c1-33-44(69-32-54-33)35-20-18-34(19-21-35)30-53-46(62)40-29-36(59)31-57(40)50(66)45(51(2,3)4)55-41(60)17-8-13-28-68-27-12-7-11-26-67-25-10-6-5-9-24-52-38-16-14-15-37-43(38)49(65)58(48(37)64)39-22-23-42(61)56-47(39)63/h14-16,18-21,32,36,39-40,45,52,59H,5-13,17,22-31H2,1-4H3,(H,53,62)(H,55,60)(H,56,61,63)/t36-,39?,40+,45-/m1/s1
    
    Canonical SMILES
    
    CC1=C(SC=N1)C2=CC=C(C=C2)CNC(=O)C3CC(CN3C(=O)C(C(C)(C)C)NC(=O)CCCCOCCCCCOCCCCCCNC4=CC=CC5=C4C(=O)N(C5=O)C6CCC(=O)NC6=O)O
- Reference Reading
  - 1. PROTAC-mediated crosstalk between E3 ligases.
    
    Steinebach, C., Kehm, H., Lindner, S., Vu, L.P., Köpff, S., Mármol, Á.L., Weiler, C., Wagner, K.G., Reichenzeller, M., Krönke, J. and Gütschow, M., 2019. Chemical Communications, 55(12), pp.1821-1824.
    
    Small-molecule heterobifunctional degraders can effectively control protein levels and are useful research tools. We assembled proteolysis targeting chimeras (PROTACs) from a cereblon (CRBN) and a von-Hippel-Lindau (VHL) ligase ligand and demonstrated a PROTAC-induced heterodimerization of the two E3 ligases leading to unidirectional and efficient degradation of CRBN.
- Preparing Stock Solutions
  - ConcentrationVolumeMass 1 mg 5 mg 10 mg
    
    1 mM 1.03 mL 5.14 mL 10.29 mL
    
    5 mM 0.21 mL 1.03 mL 2.06 mL
    
    10 mM 0.1 mL 0.51 mL 1.03 mL
    
    50 mM 0.02 mL 0.1 mL 0.21 mL

ConcentrationVolumeMass	1 mg	5 mg	10 mg
1 mM	1.03 mL	5.14 mL	10.29 mL
5 mM	0.21 mL	1.03 mL	2.06 mL
10 mM	0.1 mL	0.51 mL	1.03 mL
50 mM	0.02 mL	0.1 mL	0.21 mL

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