6-{2,4-dioxo-3-azatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-3-yl}-N-hydroxyhexanamide

• ChemBase ID: 154178
• Molecular Formular: C18H18N2O4
• Molecular Mass: 326.34652
• Monoisotopic Mass: 326.12665707
• SMILES: c1cc2cccc3c2c(c1)c(=O)n(c3=O)CCCCCC(=O)NO
• Canonical SMILES: ONC(=O)CCCCCn1c(=O)c2cccc3c2c(c1=O)ccc3
• InChI: InChI=1S/C18H18N2O4/c21-15(19-24)10-2-1-3-11-20-17(22)13-8-4-6-12-7-5-9-14(16(12)13)18(20)23/h4-9,24H,1-3,10-11H2,(H,19,21)
• InChIKey: JTDYUFSDZATMKU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{2,4-dioxo-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(13),5,7,9,11-pentaen-3-yl}-N-hydroxyhexanamide
• IUPAC Traditional name: 6-{2,4-dioxo-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(13),5,7,9,11-pentaen-3-yl}-N-hydroxyhexanamide
• Synonyms: 6-(1,3-Dioxo-1H, 3H-benzo[de]isoquinolin-2-yl)-hexanoic acid hydroxyamide; Scriptaid; Scriptide; Scriptaid; N-Hydroxy-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-hexanamide; GCK 1026; Scriptide

Database IDs

• CAS Number: 287383-59-9
• MDL Number: MFCD00386477
• PubChem SID: 162248317
• PubChem CID: 5186

CALCULATED PROPERTIES

• Acid pKa: 8.907538
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.989077
• LogD (pH = 7.4): 1.9760175
• Log P: 1.9892461
• Molar Refractivity: 88.9895 cm^3
• Polarizability: 34.517284 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble1 mg/mL; methanol: soluble
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Target: HDAC

Product Information

• Purity: ≥95%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H18N2O4

DETAILS

Sigma Aldrich - S7817

Legal Information
Sold under license of U.S. Patent No. 6,544,957.
Biochem/physiol Actions
Histone deacetylase inhibitor with lower toxicity than trichostatin A; used to enhance protein expression.

Toronto Research Chemicals - S201500

Histone deacetylase inhibitor. A cell-permeable, relatively non-toxic HDAC inhibitor that facilitates transcriptional activation (TGFβ/Smad4) in both stable and transient receptor assays in a concentration-dependent manner.

REFERENCES

• Won, J., et al.: Proc. Natl. Acad. Sci., 101, 11328 (2004)
• Su, G.H., et al.: Cancer Res., 60, 3137 (2004)
• Backs, J., et al.: J. Clin. Invest. 116, 1853 (2004)
• Fath, D., et al.: J. Biol. Chem., 281, 13612 (2004)