2,2-bis(hydroxymethyl)-1-azabicyclo[2.2.2]octan-3-one

• ChemBase ID: 154407
• Molecular Formular: C9H15NO3
• Molecular Mass: 185.2203
• Monoisotopic Mass: 185.10519335
• SMILES: C1[C@H]2C(=O)C(N(C1)CC2)(CO)CO
• Canonical SMILES: OCC1(CO)N2CC[C@@H](C1=O)CC2
• InChI: InChI=1S/C9H15NO3/c11-5-9(6-12)8(13)7-1-3-10(9)4-2-7/h7,11-12H,1-6H2
• InChIKey: RFBVBRVVOPAAFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-bis(hydroxymethyl)-1-azabicyclo[2.2.2]octan-3-one
• IUPAC Traditional name: 2,2-bis(hydroxymethyl)-1-azabicyclo[2.2.2]octan-3-one
• Synonyms: 2,2-Bishydroxymethyl-1-aza-bicyclo[2.2.2]octan-3-one; PRIMA-1

Database IDs

• CAS Number: 5608-24-2
• MDL Number: MFCD04974196
• PubChem SID: 162248546
• PubChem CID: 322968

CALCULATED PROPERTIES

• Acid pKa: 14.233833
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.2040825
• LogD (pH = 7.4): -0.91546696
• Log P: -0.7980552
• Molar Refractivity: 47.6566 cm^3
• Polarizability: 18.733315 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white to off-white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-43
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H334
• GHS Precautionary statements: P261-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C9H15NO3

DETAILS

Sigma Aldrich - P0069

Biochem/physiol Actions
PRIMA-1 is a selective re-activator of mutant p53 activity in tumor cells, and an inducer of apoptosis and inhibitor of growth of human tumors with mutant p53. Mutations in the tumor suppressor p53 take place in >50% tumor cells. PRIMA-1 selectively restores sequence-specific DNA binding and transactivational activity to mutant p53 proteins at μM concentrations. PRIMA-1 works as a re-activator of the apoptotic function of mutant p53 via conformational modulation of function-specific epitopes.