N,N'-dihydroxyoctanediamide

• ChemBase ID: 146062
• Molecular Formular: C8H16N2O4
• Molecular Mass: 204.22364
• Monoisotopic Mass: 204.111007
• SMILES: C(CCCC(=O)NO)CCC(=O)NO
• Canonical SMILES: ONC(=O)CCCCCCC(=O)NO
• InChI: InChI=1S/C8H16N2O4/c11-7(9-13)5-3-1-2-4-6-8(12)10-14/h13-14H,1-6H2,(H,9,11)(H,10,12)
• InChIKey: IDQPVOFTURLJPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N'-dihydroxyoctanediamide
• IUPAC Traditional name: N,N'-dihydroxyoctanediamide
• Synonyms: N,N′-Dihydroxyoctanediamide; SBHA; Suberoyl bis-hydroxamic acid; Suberohydroxamic acid; N1,N8-Dihydroxyoctanediamide; N,N'-Dihydroxyoctanediamide; Suberodihydroxamic Acid; Suberic Bishydroxamate; Suberoyl Bis-hydroxamic Acid; 软木肟酸

Database IDs

• CAS Number: 38937-66-5
• MDL Number: MFCD00192455
• PubChem SID: 24864150; 162240261
• PubChem CID: 5173

CALCULATED PROPERTIES

• Acid pKa: 8.606508
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.24079518
• LogD (pH = 7.4): -0.26691425
• Log P: -0.24045698
• Molar Refractivity: 49.1146 cm^3
• Polarizability: 19.263136 Å^3
• Polar Surface Area: 98.66 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 153-155 °C(lit.)

Safety Information

• German water hazard class: 3

Product Information

• Purity: 95%
• Linear Formula: [-(CH2)3CONHOH]2

DETAILS

Sigma Aldrich - 390585

Packaging
1 g in glass bottle
Biochem/physiol Actions
Suberoyl bis-hydroxamic acid (SBHA) is a Histone deacetylase (HDAC) inhibitor. SBHA inhibits the activity of HDAC1 and HDAC3 with IC50 values of 250 and 300 nM, respectively. SBHA inhibits proliferation, and induces apoptosis in several cancer cell lines. SBHA has been shown to activate Notch signaling in medullary thyroid carcinoma (MTC) cells.

Toronto Research Chemicals - S688750

Histone deacetylase inhibitor. A cell-permeable inhibitor of HDAC1 and HDAC3. Shown to suppresses the growth of proliferating keratinocytes and squamous cell carcinoma cells.

REFERENCES

• Marks, P.A., et al.: Proc.Natl. acad. Sci., 91, 10251 (1994)
• Brinkmann, H., et al.: J. Biol. Chem., 276, 22491 (1994)
• Haupt, S., et al.: J. Cell Sci., 116, 4077 (1994)
• Zhang, X., et al.: Biochem. Pharmacol., 66, 1537 (1994)
• Crighton, D., et al.: Bioch