ColupuloneCAS# 468-27-9 |
Quality Control & MSDS
3D structure
Package In Stock
Number of papers citing our products
| 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. |
||
| 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. |
||
| 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. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Lu AE58054
Catalog No.:BCC1707
CAS No.:467459-31-0
- Lu AE58054 Hydrochloride
Catalog No.:BCC1708
CAS No.:467458-02-2
- Nootkatone
Catalog No.:BCN5517
CAS No.:4674-50-4
- Diphenyleneiodonium chloride
Catalog No.:BCC6670
CAS No.:4673-26-1
- 17-DMAG (Alvespimycin) HCl
Catalog No.:BCC1175
CAS No.:467214-21-7
- Alvespimycin
Catalog No.:BCC1346
CAS No.:467214-20-6
- Theaflavin
Catalog No.:BCN5419
CAS No.:4670-05-7
- Rehmannic acid
Catalog No.:BCN4632
CAS No.:467-81-2
- Coronaridine
Catalog No.:BCN3762
CAS No.:467-77-6
- Hecogenin
Catalog No.:BCN5408
CAS No.:467-55-0
- N-Methylcorydiniumiodide
Catalog No.:BCN7873
CAS No.:4668-64-6
- Z-Asp-OMe
Catalog No.:BCC2792
CAS No.:4668-42-2
- Lupulon
Catalog No.:BCC8204
CAS No.:468-28-0
- Mesembrenone
Catalog No.:BCN3753
CAS No.:468-54-2
- Drimenol
Catalog No.:BCN7224
CAS No.:468-68-8
- Orphenadrine Citrate
Catalog No.:BCC4572
CAS No.:4682-36-4
- Norscopolamine
Catalog No.:BCN3983
CAS No.:4684-28-0
- Picrinine
Catalog No.:BCN5518
CAS No.:4684-32-6
- Dihydrocorynantheine
Catalog No.:BCN3747
CAS No.:4684-43-9
- 3-Benzofurancarboxaldehyde
Catalog No.:BCC8622
CAS No.:4687-25-6
- Cimilactone A
Catalog No.:BCN7948
CAS No.:468733-06-4
- BMS-536924
Catalog No.:BCC1177
CAS No.:468740-43-4
- Hamamelitannin
Catalog No.:BCC8182
CAS No.:469-32-9
- Cycloeucalenol
Catalog No.:BCN5519
CAS No.:469-39-6
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.
