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401250-M

Millipore

Ilimaquinone

A cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties.

Synonym(s):

Ilimaquinone, 3-[(Decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-napthyl)methyl]-2-hydroxy-5-methoxybenzoquinone, IQ

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About This Item

Empirical Formula (Hill Notation):
C22H30O4
CAS Number:
Molecular Weight:
358.47
UNSPSC Code:
12352200

Quality Level

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

red

solubility

DMSO: 200 mg/mL

storage temp.

−20°C

InChI

1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18+,21+,22+/m0/s1

InChI key

JJWITJNSXCXULM-YVUMSICPSA-N

General description

A cell-permeable marine sponge metabolite that induces complete and reversible breakdown of Golgi membranes into smaller vesicular structures, possibly through the activation of heterotrimeric G-proteins. Blocks protein transport at the cis-Golgi and depolymerizes microtubules. Also possesses anti-HIV activity and the ability to inhibit the cytotoxicity of ricin and diphtheria toxin.
A cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties. Induces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules. Inhibits cellular methylations through its interaction with S-adenosylhomocysteinase. Blocks the cytotoxicity of ricin and diphtheria toxin. Acts as an inhibitor of the RNase H activity of HIV-1.

Biochem/physiol Actions

Primary Target
Induces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules.

Warning

Toxicity: Standard Handling (A)

Other Notes

Radeke, H.S., et al. 1999. Chem. Biol. 6, 639.
Radeke, H.S., and Snapper, M.L. 1998. Bioorg. Med. Chem.6, 1227.
Jamora, C., et al. 1997. Cell 91, 617.
Nambiar, M.P., and Wu, H.C. 1995. Exp. Cell Res. 219, 671.
Loya, S., and Hizi, A. 1993. J. Biol. Chem. 268, 9323.
Takizawa, P.A., et al. 1993. Cell 73, 1079.
Veit, B., et al. 1993. J. Cell Biol. 122, 1197.

Legal Information

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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