ColupuloneCAS# 468-27-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 468-27-9 | SDF | Download SDF |
PubChem ID | 373677 | Appearance | Powder |
Formula | C25H36O4 | M.Wt | 400.55 |
Type of Compound | Miscellaneous | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one | ||
SMILES | CC(C)C(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O | ||
Standard InChIKey | UNCDMWKTFLUPHZ-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C25H36O4/c1-15(2)9-10-19-22(27)20(21(26)18(7)8)24(29)25(23(19)28,13-11-16(3)4)14-12-17(5)6/h9,11-12,18,27-28H,10,13-14H2,1-8H3 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | 1. Colupulone can increase cytochrome P450IIB and P450IIIA steady-state mRNA levels. 2. Colupulone is an inducer of hepatic cytochrome P-4503A . 3. Colupulone has antibacterial effects. |
Targets | P450 (e.g. CYP17) | Calcium Channel | Sodium Channel | Potassium Channel | Antifection |
Colupulone Dilution Calculator
Colupulone Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.4966 mL | 12.4828 mL | 24.9657 mL | 49.9313 mL | 62.4142 mL |
5 mM | 0.4993 mL | 2.4966 mL | 4.9931 mL | 9.9863 mL | 12.4828 mL |
10 mM | 0.2497 mL | 1.2483 mL | 2.4966 mL | 4.9931 mL | 6.2414 mL |
50 mM | 0.0499 mL | 0.2497 mL | 0.4993 mL | 0.9986 mL | 1.2483 mL |
100 mM | 0.025 mL | 0.1248 mL | 0.2497 mL | 0.4993 mL | 0.6241 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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Structural basis of human pregnane X receptor activation by the hops constituent colupulone.[Pubmed:18768384]
Mol Pharmacol. 2008 Dec;74(6):1512-20.
Hops extracts are used to alleviate menopausal symptoms and as an alternative to hormone replacement therapy, but they can produce potentially harmful drug-drug interactions. The nuclear xenobiotic receptor pregnane X receptor (PXR) is promiscuously activated by a range of structurally distinct chemicals. It has a key role in the transcriptional regulation of genes that encode xenobiotic metabolism enzymes. In this study, hops extracts are shown to induce the expression of numerous drug metabolism and excretion proteins. The beta-bitter acid Colupulone is demonstrated to be a bioactive component and direct activator of human PXR. The 2.8-A resolution crystal structure of the ligand binding domain of human PXR in complex with Colupulone was elucidated, and Colupulone was observed to bind in a single orientation stabilized by both van der Waals and hydrogen bonding contacts. The crystal structure also indicates that related alpha- and beta-bitter acids have the capacity to serve as PXR agonists as well. Taken together, these results reveal the structural basis for drug-drug interactions mediated by Colupulone and related constituents of hops extracts.
The effect of colupulone (a HOPS beta-acid) on hepatic cytochrome P-450 enzymatic activity in the rat.[Pubmed:7959454]
Food Chem Toxicol. 1994 Nov;32(11):1007-14.
Colupulone, a component of hops, was examined for its ability to alter rat hepatic cytochrome P-450 enzymatic activity, expression of hepatic cytochrome P-450 mRNA, and in vitro promutagen activation. Colupulone was fed to male Sprague-Dawley rats for 5 days at 0.36% in the modified AIN 76 diet. Three cytochrome P-450 enzymatic activities were measured, and the corresponding steady-state mRNA levels were examined by Northern blot hybridization. Colupulone increased cytochrome P450IIB and P450IIIA steady-state mRNA levels. In vitro promutagen activation was measured in the Ames assay using liver homogenates from each treatment group. Colupulone treatment did not alter the ex vivo cytochrome P-450-mediated activation of aflatoxin B1 or benzo[a]pyrene to their mutagenic forms. The effect of long-term Colupulone administration on in vivo cytochrome P-450 enzymatic activity remains to be determined.
Factors affecting antibacterial activity of hop compounds and their derivatives.[Pubmed:1517174]
J Appl Bacteriol. 1992 Apr;72(4):327-34.
The antibacterial effect of weak acids derived from the hop plant (Humulus lupulus L.) increased with decreasing pH. Analysis of the minimum inhibitory concentration of such compounds against Lactobacillus brevis IFO 3960 over pH 4-7 suggests that undissociated molecules were mainly responsible for inhibition of bacterial growth. The antibacterial activity of trans-isohumulone was ca 20 times greater than that of humulone, 11 times greater than that of Colupulone and nine times greater than that of trans-humulinic acid when the degree of ionization was taken into account. Monovalent cations (K+, Na+, NH4+, Rb+, Li+) stimulated antibacterial activity of trans-isohumulone but the effect was smaller than that observed with H+. The response to divalent cations varied: Ca2+ had little effect on antibacterial activity, whereas Mg2+ reduced activity. Lipid materials and beta-cyclodextrin also antagonized the antibacterial action of trans-isohumulone.