| Identification | Back Directory | [Name]
ILIMAQUINONE | [CAS]
71678-03-0 | [Synonyms]
IQ
ILIMAQUINONE
illimaquinone
(-)-Ilimaquinine
(-)-ILIMAQUINONE
5-Epiilimaquinone
Ilimaquinone - CAS 71678-03-0 - Calbiochem
3-[(DECAHYDRO-1B,2B,4AB-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE
3-[(decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone
2-[[(1R,8aα)-1,2β,4aβ-Trimethyl-5-methylenedecalin-1α-yl]methyl]-3-hydroxy-6-methoxy-1,4-benzoquinone
3-[(DECAHYDRO-1BETA,2BETA,4A-BETA-TRIMETHYL-5-METHYLENE-1-NAPTHYL)METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE
3-[(DECAHYDRO-1BETA,2BETA,4A-BETA-TRIMETHYL-5-METHYLENE-1-NAPHTHYL)-METHYL]-2-HYDROXY-5-METHOXYBENZOQUINONE
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
3-[[[(1R,8aα)-Decahydro-1,2β,4aβ-trimethyl-5-methylenenaphthalen]-1α-yl]methyl]-2-hydroxy-5-methoxy-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-2,5-cyclohexadiene-1,4-dione
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- | [Molecular Formula]
C22H30O4 | [MDL Number]
MFCD00274432 | [MOL File]
71678-03-0.mol | [Molecular Weight]
358.47 |
| Chemical Properties | Back Directory | [Melting point ]
108-110℃ (pentane ) | [alpha ]
D23 -23.2° (c = 1.12 in CHCl3) | [Boiling point ]
478.4±45.0 °C(Predicted) | [density ]
1.14±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
DMSO: Soluble; Ethanol: Soluble; Hexane: Soluble; Methanol: Soluble | [form ]
Red solid | [pka]
2.92±0.50(Predicted) | [color ]
Light yellow to brown | [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 | [InChIKey]
JJWITJNSXCXULM-YVUMSICPSA-N |
| Hazard Information | Back Directory | [Description]
Ilimaquinone is a natural sesquiterpene quinone that has antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties. In mammalian cells, 25 μM ilimaquinone reversibly induces vesiculation of Golgi membranes, blocking the secretory pathway. It inhibits the conversion of S-adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase (IC50 = 40 μM). Ilimaquinone also inhibits DNA polymerase β and dual specificity phosphatase Cdc25B (IC50 = 45.2 and 92 μM, respectively) and, at 10 μM, activates gene expression through hypoxia-inducible factor-1. | [Uses]
Biological probe for intracellular communications and vesicle-mediated transport. | [Definition]
ChEBI: A natural product found in Dactylospongia elegans. | [General Description]
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 TargetInduces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules. | [References]
[1] H S RADEKE. Interactions of (-)-ilimaquinone with methylation enzymes: implications for vesicular-mediated secretion.[J]. Chemistry & biology, 1999, 6 9: 639-647. DOI: 10.1016/s1074-5521(99)80115-x
[2] P A TAKIZAWA. Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone.[J]. Cell, 1993, 73 6: 1079-1090. DOI: 10.1016/0092-8674(93)90638-7
[3] VéRONIQUE CRUCIANI Svein O M Edward Leithe. Ilimaquinone inhibits gap-junctional communication prior to Golgi fragmentation and block in protein transport[J]. Experimental cell research, 2003, 287 1: Pages 130-142. DOI: 10.1016/s0014-4827(03)00124-1
[4] BYUNG GYU KIM . A new structural class of S-adenosylhomocysteine hydrolase inhibitors[J]. Bioorganic & Medicinal Chemistry, 2009, 17 18: Pages 6707-6714. DOI: 10.1016/j.bmc.2009.07.061
[5] SHUGENG CAO. Marine Sesquiterpenoids that Inhibit the Lyase Activity of DNA Polymerase β[J]. Journal of Natural Products , 2004, 67 10: 1716-1718. DOI: 10.1021/np049849+
[6] LIN DU Dale G N Yu Dong Zhou*. Inducers of Hypoxic Response: Marine Sesquiterpene Quinones Activate HIF-1[J]. Journal of Natural Products , 2013, 76 6: 1175-1181. DOI: 10.1021/np400320r |
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