Ilimaquinone is a marine sponge metabolite that exerts anti-tumor activity through the GADD153-mediated signaling pathway. Ilimaquinone induces vesiculation of the Golgi apparatus. Ilimaquinone has antiviral, antibacterial and anti-inflammatory activities.

Physicochemical Properties

Molecular Formula	C22H30O4
Molecular Weight	358.47
Exact Mass	358.214
CAS #	71678-03-0
PubChem CID	72291
Appearance	Light yellow to brown solid powder
Density	1.1±0.1 g/cm3
Boiling Point	478.4±45.0 °C at 760 mmHg
Flash Point	159.9±22.2 °C
Vapour Pressure	0.0±2.7 mmHg at 25°C
Index of Refraction	1.549
LogP	6.38
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Heavy Atom Count	26
Complexity	728
Defined Atom Stereocenter Count	4
SMILES	C[C@H]1CC[C@]2([C@H]([C@]1(C)CC3=C(C(=O)C=C(C3=O)OC)O)CCCC2=C)C
InChi Key	JJWITJNSXCXULM-YVUMSICPSA-N
InChi Code	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
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
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Ilimaquinone has the ability to inhibit the growth of many cancer cell lines in a concentration-dependent manner. These cell lines include PC-3 and LNCaP prostate cancers, A549 non-small cell lung cancer, and Hep3B cells from hepatocellular carcinoma. With GI50s of 2.6 μM, 5.8, 4.6, 4.9, 4.1, and 12.0 μM, respectively, imimaquinone (0.3-30 μM; 48 hours) suppresses the proliferation of PC-3 cells, DU145, LNCaP, MG63, A549, and Hep3B cells[1].
ln Vivo	In male Sprague-Dawley rats, imimaquinone had high plasma clearance (2.95±0.53 L/h/kg) after oral administration (10 mg/kg), resulting in terminal elimination half-lives (T1/2=1.2±0.3 h)[2].
Cell Assay	Cell Viability Assay[1] Cell Types: Prostate cancer PC-3 cells Tested Concentrations: 0.3, 1, 3, 10, and 30 μM Incubation Duration: 48 hrs (hours) Experimental Results: Inhibited the proliferation of PC-3 cells in a concentration-dependent manner.
References	[1]. Ilimaquinone, a Marine Sponge Metabolite, Displays Anticancer Activity via GADD153-mediated Pathway. Eur J Pharmacol. 2007 Feb 5;556(1-3):45-54. [2]. Stereo-Selective Pharmacokinetics of Ilimaquinone Epimers Extracted From a Marine Sponge in Rats. Mar Drugs. 2019 Mar 17;17(3):171.
Additional Infomation	Ilimaquinone is a prenylquinone and a member of monohydroxy-1,4-benzoquinones. It has a role as a metabolite. Ilimaquinone has been reported in Verongula rigida, Dactylospongia elegans, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.7896 mL	13.9482 mL	27.8963 mL
	5 mM	0.5579 mL	2.7896 mL	5.5793 mL
	10 mM	0.2790 mL	1.3948 mL	2.7896 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.