345887

Ginkgolic Acid (15:1)

A cell-permeable anacardic acid analog that inhibits protein SUMO .

• Synonym(s): Ginkgolic Acid (15:1), (Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, SUMOylation Inhibitor, HAT Inhibitor VI, Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, SUMOylation Inhibitor, (Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, HAT Inhibitor VI
• Empirical Formula (Hill Notation): C₂₂H₃₄O₃
• CAS Number: 22910-60-7
• Molecular Weight: 346.50
• UNSPSC Code: 12352106
• NACRES: NA.77
• MDL number: MFCD03093717
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: 100 mg/mL, ethanol: 100 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: Oc1c(c(ccc1)CCCCCCC\C=C/CCCCCC)C(=O)O
• InChI: 1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7-
• InChI key: YXHVCZZLWZYHSA-FPLPWBNLSA-N

Description

General description

A cell-permeable anacardic acid (Cat. No. 172050) analog that inhibits protein SUMO modification (IC₅₀ = 3.0 µM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 and interfering with E1-SUMO intermediate formation independent of E1 active site cysteine. Both ginkgolic acid and anacardic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins, including p53, in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although both compounds are shown to inhibit histone lysine acetylation by PCAF in cell-free acetylase assays. Also available as a 25 mM solution in DMSO (Cat. No. 5.08197).

Packaging

Packaged under inert gas

Preparation Note

Following intitial thaw, aliquot and freeze (-20°C).

Other Notes

Fukuda, I., et al. 2009. Chem. Biol.16, 133.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317,H413
• pcodes: P261 - P272 - P273 - P280 - P302 + P352 - P333 + P313
• Hazard Classifications: Aquatic Chronic 4 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: 509.9 °F - (calculated)
• flash_point_c: 265.5 °C - (calculated)