N-hydroxy-N'-(2H5)phenyloctanediamide

• ChemBase ID: 177897
• Molecular Formular: C14H20N2O3
• Molecular Mass: 264.3202
• Monoisotopic Mass: 264.14739251
• SMILES: c1ccccc1NC(=O)CCCCCCC(=O)NO
• Canonical SMILES: ONC(=O)CCCCCCC(=O)Nc1ccccc1
• InChI: InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)
• InChIKey: WAEXFXRVDQXREF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-hydroxy-N'-(^2H₅)phenyloctanediamide
• IUPAC Traditional name: N-hydroxy-N'-(^2H₅)phenyloctanediamide
• Synonyms: SAHA-d5; N-Hydroxy-N’-phenyl-d5-octanediamide; Zolinza-d5; Vorinostat-d5; Suberoylanilide-d5 Hydroxamic Acid

Database IDs

• PubChem SID: 164233807
• PubChem CID: 25235331

CALCULATED PROPERTIES

• Acid pKa: 8.907536
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.0038002
• LogD (pH = 7.4): 1.9907405
• Log P: 2.0039692
• Molar Refractivity: 73.8051 cm^3
• Polarizability: 28.12008 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: White Solid
• Melting Point: 161-162°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S688702

A potent, selective, cell permeable histone deacetylase inhibitor (HDAC). Displays anti-angiogenic activity by interfering with VEGF signaling in human umbilical vein endothelial cells (HUVECs). Induces differentiation in uman breast cancer cells.

REFERENCES

• Richon, V.M., et al.: Proc. Natl. Acad.Sci. USA, 95, 3003 (1988)
• Munster, P.N., et al.: Cancer Res., 61, 8492 (1988)
• Deroanne, C.F., et al.: Oncogene, 21, 247 (1988)