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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C22H34O3
CAS Number:
22910-60-7
Molecular Weight:
346.50
UNSPSC Code:
12352106
NACRES:
NA.77
MDL number:
MFCD03093717

Key Documents

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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

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

Quality Level

100

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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)

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317,H413

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)

Certificates of Analysis (COA)

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Wenjun Wang et al.
Journal of agricultural and food chemistry, 67(36), 10097-10106 (2019-08-17)
Ginkgolic acids (GAs) are found in the leaves, nuts, and testa of Ginkgo biloba and have been reported to exhibit antitumor, antibacterial, and pro-apoptotic activities. However, their role in mitochondrial function is still unclear. Our previous study showed that genes

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