2-[2,6-bis(propan-2-yl)phenyl]-5-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 154136
• Molecular Formular: C20H21NO3
• Molecular Mass: 323.38564
• Monoisotopic Mass: 323.15214354
• SMILES: CC(C)c1cccc(c1N1C(=O)c2ccc(cc2C1=O)O)C(C)C
• Canonical SMILES: Oc1ccc2c(c1)C(=O)N(C2=O)c1c(cccc1C(C)C)C(C)C
• InChI: InChI=1S/C20H21NO3/c1-11(2)14-6-5-7-15(12(3)4)18(14)21-19(23)16-9-8-13(22)10-17(16)20(21)24/h5-12,22H,1-4H3
• InChIKey: LAKWINYVWJPHQW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2,6-bis(propan-2-yl)phenyl]-5-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-(2,6-diisopropylphenyl)-5-hydroxyisoindole-1,3-dione
• Synonyms: 2-[2,6-bis(1-Methylethyl)phenyl]-5-hydroxy-1H-isoindole-1,3(2H)-dione; 5-Hydroxy-2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione; 5HPP-33

Database IDs

• CAS Number: 105624-86-0
• MDL Number: MFCD03085294
• PubChem SID: 162248275
• PubChem CID: 11723708

CALCULATED PROPERTIES

• Acid pKa: 7.874298
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.7596936
• LogD (pH = 7.4): 4.6369615
• Log P: 4.7615104
• Molar Refractivity: 94.3516 cm^3
• Polarizability: 35.584965 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H21NO3

DETAILS

Sigma Aldrich - H9415

Biochem/physiol Actions
5HPP-33 is a thalidomide derivative which was reported to be active as anticancer agent through stabilization of the microtubules. 5HPP-33 has shown inhibition of cell proliferation of both estrogen-dependent (MCF-7) and estrogen-independent (MDA-MB-231) breast cancer cells as well as other cell lines. A study in tubulin forming assay reported that 5HPP-33 acts as a microtubule formation inhibitor (IC50=810 nM).