71678-03-0

71678-03-0 structure

Name: Ilimaquinone
Chemical Name: 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
CAS Number: 71678-03-0
Molecular Formula: C₂₂H₃₀O₄
Molecular Weight: 358.471
Catalog: Signaling Pathways Anti-infection Bacterial
Create Date: 2018-09-13 20:14:30
Modify Date: 2026-07-16 11:51:25
Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway. Ilimaquinone can induce vesiculation of the Golgi apparatus[1]. Ilimaquinone exerts anti-HIV, anti-microbial, anti-inflammatory, and effects[2].

Name	3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms	(-)-Ilimaquinine 3-[(DECAHYDRO-1BETA,2BETA,4ALPHA-BETA-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE 3-[[(1R,8aα)-Decahydro-1,2β,4aβ-trimethyl-5-methylenenaphthalene-1α-yl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione 5-iilimaquinone 2-Hydroxy-5-methoxy-3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylenedecahydro-1-naphthalenyl]methyl}-1,4-benzoquinone 3-[(decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone Ilimaquinone, Cytoplasmic microtubule inhibitor illimaquinone Illimaquinone Imaquinone ILIMAQUINONE MFCD00274432 3-[[(1R,2S,4aS,8aS)-Decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione 2-[[(1R,8aα)-1,2β,4aβ-Trimethyl-5-methylenedecalin-1α-yl]methyl]-3-hydroxy-6-methoxy-1,4-benzoquinone (-)-ILIMAQUINONE 2,5-CYCLOHEXADIENE-1,4-DIONE,3-[[(1R,2S,4AS,8AS)-DECAHYDRO-1,2,4A-TRIMETHYL-5-METHYLENE-1-NAPHTHALENYL] METHYL]-2-HYDROXY-5-METHOXY Ilimaquinone - - Calbiochem 3-[(DECAHYDRO-1BETA,2BETA,4A-BETA-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)-METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE 2-hydroxy-5-methoxy-3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidenedecahydronaphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione 3-[[[(1R,8aα)-Decahydro-1,2β,4aβ-trimethyl-5-methylenenaphthalen]-1α-yl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione 3-[(DECAHYDRO-1BETA,2BETA,4A-BETA-TRIMETHYL-5-METHYLENE-1-NAPTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE 3-[(DECAHYDRO-1B,2B,4AB-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE

Description	Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway. Ilimaquinone can induce vesiculation of the Golgi apparatus[1]. Ilimaquinone exerts anti-HIV, anti-microbial, anti-inflammatory, and effects[2].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Anti-infection >> HIV Research Areas >> Infection Research Areas >> Inflammation/Immunology Signaling Pathways >> Anti-infection >> Bacterial
In Vitro	Ilimaquinone induces a concentration-dependent anti-proliferative effect in several types of cancer cell lines, including prostate cancer PC-3 and LNCaP, non-small cell lung cancer A549 and hepatocellular carcinoma Hep3B cells. Ilimaquinone (0.3-30 μM; 48 hours) inhibits the proliferation of PC-3 cells, DU145, LNCaP, MG63, A549, Hep3B cells with GI50s of 2.6 μM, 5.8, 4.6, 4.9, 4.1, 12.0μM, respectively[1]. Cell Viability Assay[1] Cell Line: Prostate cancer PC-3 cells Concentration: 0.3, 1, 3, 10, and 30 μM Incubation Time: 48 hours Result: Inhibited the proliferation of PC-3 cells in a concentration-dependent manner.
In Vivo	Ilimaquinone exhibits terminal elimination half-lives (T1/2=1.2±0.3 h) due to high plasma clearance (2.95±0.53 L/h/kg) following oral administration (10 mg/kg) in male Sprague-Dawley rats[2].
References	[1]. Pin-Hsuan Lu, et al. Ilimaquinone, a Marine Sponge Metabolite, Displays Anticancer Activity via GADD153-mediated Pathway. Eur J Pharmacol. 2007 Feb 5;556(1-3):45-54. [2]. Heebin Son, et al. Stereo-Selective Pharmacokinetics of Ilimaquinone Epimers Extracted From a Marine Sponge in Rats. Mar Drugs. 2019 Mar 17;17(3):171.

Density	1.1±0.1 g/cm3
Boiling Point	478.4±45.0 °C at 760 mmHg
Molecular Formula	C₂₂H₃₀O₄
Molecular Weight	358.471
Flash Point	159.9±22.2 °C
Exact Mass	358.214417
PSA	63.60000
LogP	6.38
Vapour Pressure	0.0±2.7 mmHg at 25°C
Index of Refraction	1.549

WGK Germany	3

Precursor 8
121994-56-7 41722-49-0 2441-46-5 86489-89-6
213026-15-4 213026-18-7 583-63-1 3117-03-1
DownStream 1
121994-56-7

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