Ilimaquinone

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 463665

CAS#: 71678-03-0

Description: Ilimaquinone is a natural irreversible inactivator of Mycobacterium tuberculosis shikimate kinase (MtSK), inducing the apoptotic cell death of cancer cells by reducing pyruvate dehydrogenase kinase 1 (PDK1) activity.


Chemical Structure

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Ilimaquinone
CAS# 71678-03-0

Theoretical Analysis

MedKoo Cat#: 463665
Name: Ilimaquinone
CAS#: 71678-03-0
Chemical Formula: C22H30O4
Exact Mass: 358.2144
Molecular Weight: 358.478
Elemental Analysis: C, 73.71; H, 8.44; O, 17.85

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Ilimaquinone;

IUPAC/Chemical Name: 2-hydroxy-5-methoxy-3-(((1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylenedecahydronaphthalen-1-yl)methyl)cyclohexa-2,5-diene-1,4-dione

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

SMILES Code: O=C1C(OC)=CC(C(O)=C1C[C@@]2(C)[C@H](CCCC3=C)[C@]3(C)CC[C@@H]2C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 358.478 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Shikov AN, Flisyuk EV, Obluchinskaya ED, Pozharitskaya ON. Pharmacokinetics of Marine-Derived Drugs. Mar Drugs. 2020 Nov 9;18(11):557. doi: 10.3390/md18110557. PMID: 33182407; PMCID: PMC7698100.

2: Kwak CH, Jin L, Han JH, Han CW, Kim E, Cho M, Chung TW, Bae SJ, Jang SB, Ha KT. Ilimaquinone Induces the Apoptotic Cell Death of Cancer Cells by Reducing Pyruvate Dehydrogenase Kinase 1 Activity. Int J Mol Sci. 2020 Aug 21;21(17):6021. doi: 10.3390/ijms21176021. PMID: 32825675; PMCID: PMC7504051.

3: Lin CW, Bai LY, Su JH, Chiu CF, Lin WY, Huang WT, Shih MC, Huang YT, Hu JL, Weng JR. Ilimaquinone Induces Apoptosis and Autophagy in Human Oral Squamous Cell Carcinoma Cells. Biomedicines. 2020 Aug 20;8(9):296. doi: 10.3390/biomedicines8090296. PMID: 32825464; PMCID: PMC7555415.

4: Son Y, Lim D, Park S, Song IS, Kim JH, Shin S, Jang H, Liu KH, O Y, Song GY, Kang W, Cho YS, Na M, Chung H, Oh S. Ilimaquinone inhibits neovascular age- related macular degeneration through modulation of Wnt/β-catenin and p53 pathways. Pharmacol Res. 2020 Nov;161:105146. doi: 10.1016/j.phrs.2020.105146. Epub 2020 Aug 16. PMID: 32814173.

5: van Stuijvenberg J, Proksch P, Fritz G. Targeting the DNA damage response (DDR) by natural compounds. Bioorg Med Chem. 2020 Feb 15;28(4):115279. doi: 10.1016/j.bmc.2019.115279. Epub 2020 Jan 8. PMID: 31980363.

6: Son H, Noh K, Park I, Na M, Oh S, Shin BS, Kang W. Stereo-Selective Pharmacokinetics of Ilimaquinone Epimers Extracted from a Marine Sponge in Rats. Mar Drugs. 2019 Mar 17;17(3):171. doi: 10.3390/md17030171. PMID: 30884884; PMCID: PMC6472033.

7: Son H, Noh K, Kang C, Na M, Oh S, Song IS, Kang W. HPLC-MS/MS analysis of ilimaquinone and its application in a pharmacokinetic study in rats. J Pharm Biomed Anal. 2019 Mar 20;166:291-294. doi: 10.1016/j.jpba.2019.01.030. Epub 2019 Jan 17. PMID: 30684930.

8: Ju E, Latif A, Kong CS, Seo Y, Lee YJ, Dalal SR, Cassera MB, Kingston DGI. Antimalarial activity of the isolates from the marine sponge Hyrtios erectus against the chloroquine-resistant Dd2 strain of Plasmodium falciparum. Z Naturforsch C J Biosci. 2018 Sep 25;73(9-10):397-400. doi: 10.1515/znc-2018-0025. PMID: 29813035.

9: Simithy J, Fuanta NR, Hobrath JV, Kochanowska-Karamyan A, Hamann MT, Goodwin DC, Calderón AI. Mechanism of irreversible inhibition of Mycobacterium tuberculosis shikimate kinase by ilimaquinone. Biochim Biophys Acta Proteins Proteom. 2018 May-Jun;1866(5-6):731-739. doi: 10.1016/j.bbapap.2018.04.007. Epub 2018 Apr 12. PMID: 29654976.

10: Bonneau N, Chen G, Lachkar D, Boufridi A, Gallard JF, Retailleau P, Petek S, Debitus C, Evanno L, Beniddir MA, Poupon E. An Unprecedented Blue Chromophore Found in Nature using a "Chemistry First" and Molecular Networking Approach: Discovery of Dactylocyanines A-H. Chemistry. 2017 Oct 17;23(58):14454-14461. doi: 10.1002/chem.201702336. Epub 2017 Sep 19. PMID: 28815818.

11: Kaplan HZ, Rendina VL, Kingsbury JS. General Methodologies Toward cis-Fused Quinone Sesquiterpenoids. Enantiospecific Synthesis of the epi-Ilimaquinone Core Featuring Sc-Catalyzed Ring Expansion. Molecules. 2017 Jun 24;22(7):1041. doi: 10.3390/molecules22071041. PMID: 28672821; PMCID: PMC6152358.

12: Kiem PV, Huyen LT, Hang DT, Nhiem NX, Tai BH, Anh HL, Cuong PV, Quang TH, Minh CV, Dau NV, Kim YA, Subedi L, Kim SY, Kim SH. Sesquiterpene derivatives from marine sponge Smenospongia cerebriformis and their anti-inflammatory activity. Bioorg Med Chem Lett. 2017 Apr 1;27(7):1525-1529. doi: 10.1016/j.bmcl.2017.02.040. Epub 2017 Feb 21. PMID: 28262525.

13: Klayman LM, Wedegaertner PB. Inducible Inhibition of Gβγ Reveals Localization-dependent Functions at the Plasma Membrane and Golgi. J Biol Chem. 2017 Feb 3;292(5):1773-1784. doi: 10.1074/jbc.M116.750430. Epub 2016 Dec 19. PMID: 27994056; PMCID: PMC5290951.

14: Ratovitski EA. Tumor Protein (TP)-p53 Members as Regulators of Autophagy in Tumor Cells upon Marine Drug Exposure. Mar Drugs. 2016 Aug 16;14(8):154. doi: 10.3390/md14080154. PMID: 27537898; PMCID: PMC4999915.

15: Chaikina EL, Utkina NK, Anisimov MM. Influence of Merosesquiterpenoids from Marine Sponges on Seedling Root Growth of Agricultural Plants. Nat Prod Commun. 2016 Jan;11(1):11-2. PMID: 26996006.

16: Lee HY, Chung KJ, Hwang IH, Gwak J, Park S, Ju BG, Yun E, Kim DE, Chung YH, Na M, Song GY, Oh S. Activation of p53 with ilimaquinone and ethylsmenoquinone, marine sponge metabolites, induces apoptosis and autophagy in colon cancer cells. Mar Drugs. 2015 Jan 16;13(1):543-57. doi: 10.3390/md13010543. PMID: 25603347; PMCID: PMC4306951.

17: Do MT, Na M, Kim HG, Khanal T, Choi JH, Jin SW, Oh SH, Hwang IH, Chung YC, Kim HS, Jeong TC, Jeong HG. Ilimaquinone induces death receptor expression and sensitizes human colon cancer cells to TRAIL-induced apoptosis through activation of ROS-ERK/p38 MAPK-CHOP signaling pathways. Food Chem Toxicol. 2014 Sep;71:51-9. doi: 10.1016/j.fct.2014.06.001. Epub 2014 Jun 12. PMID: 24930757.

18: Park S, Yun E, Hwang IH, Yoon S, Kim DE, Kim JS, Na M, Song GY, Oh S. Ilimaquinone and ethylsmenoquinone, marine sponge metabolites, suppress the proliferation of multiple myeloma cells by down-regulating the level of β-catenin. Mar Drugs. 2014 May 28;12(6):3231-44. doi: 10.3390/md12063231. PMID: 24879546; PMCID: PMC4071574.

19: Du L, Zhou YD, Nagle DG. Inducers of hypoxic response: marine sesquiterpene quinones activate HIF-1. J Nat Prod. 2013 Jun 28;76(6):1175-81. doi: 10.1021/np400320r. Epub 2013 Jun 3. PMID: 23731014; PMCID: PMC3718637.

20: Kumar R, Subramani R, Aalbersberg W. Three bioactive sesquiterpene quinones from the Fijian marine sponge of the genus Hippospongia. Nat Prod Res. 2013;27(16):1488-91. doi: 10.1080/14786419.2012.722086. Epub 2012 Sep 10. PMID: 22963320.