≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Praeruptorin B is an inhibitor of sterol regulatory element-binding proteins (SREBPs) .
In Vitro
Praeruptorin B inhibits the SREBPs activity and decreases intracellular lipid levels. Praeruptorin B is found to powerfully decrease the SRE-luciferase activity, and this effect is dose dependent. Praeruptorin B shows negligible cytotoxicity, even at the higher concentration. Praeruptorin B also significantlytly down-regulates the expression of SREBP-1c and SREBP-2. Praeruptorin B also exhibits significant inhibition on the activity of UGT1A9. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
The mice treated with Praeruptorin B (50 mg/kg) are significantly lighter than the vehicle treated mice, although they are still heavier than the chow diet-fed mice, suggesting that Praeruptorin B can ameliorate diet-induced obesity (DIO). More importantly, the fat/lean and fat/body-weight ratios are obviously dropped at the same dosage of Praeruptorin B treated mice. It is also showed that the serum TC and TG levels of Praeruptorin B treated mice are significantly lower than those of the HFD-fed mice. Praeruptorin B increases HDL-c and decreases LDL-c similar as lovastatin. In addition, compared with vehicle treated mice, Praeruptorin B significantly lowers the level of TC and TG in liver, comparable to lovastatin. The staining results reveal that Praeruptorin B-treated mice exhibit less lipid accumulation than that of vehicle treated mice. The elevated fasting blood glucose and insulin in HFD-fed mice are significantly reduced by Praeruptorin B . MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:SREBP
| Canonical Smiles | CC=C(C)C(=O)OC1C(C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)OC(=O)C(=CC)C |
|---|---|
| IUPAC Name | [(9S,10S)-8,8-dimethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (Z)-2-methylbut-2-enoate |
| InChIKey | PNTWXEIQXBRCPS-UWOGZXHISA-N |
| INCHI | 1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7-,14-8-/t20-,21-/m0/s1 |
| Isomeric SMILES | C/C=C(/C)\C(=O)O[C@@H]1[C@@H](C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)OC(=O)/C(=C\C)/C |
| Alternate CAS | 73069-28-0,73069-26-8 |
| PubChem CID | 25717254 |
| MeSH Entry Terms | anomalin;anomalin, (9alpha(E),10alpha(E));anomalin, (9S-(9alpha(Z),10alpha(Z)))-isomer;anomalin, (Z,Z)-isomer;praeruptorin B |
| Molecular Weight | 426.46 |
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Coumarins and derivatives |
| Subclass | Pyranocoumarins |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Angular pyranocoumarins |
| Alternative Parents | Pyranochromenes 2,2-dimethyl-1-benzopyrans Pyranones and derivatives Fatty acid esters Alkyl aryl ethers Dicarboxylic acids and derivatives Benzenoids Heteroaromatic compounds Enoate esters Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Angular pyranocoumarin - Pyranochromene - 2,2-dimethyl-1-benzopyran - Chromane - Benzopyran - 1-benzopyran - Alkyl aryl ether - Fatty acid ester - Pyranone - Dicarboxylic acid or derivatives - Pyran - Fatty acyl - Benzenoid - Heteroaromatic compound - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Lactone - Carboxylic acid ester - Oxacycle - Ether - Carboxylic acid derivative - Organoheterocyclic compound - Organic oxide - Organooxygen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. |
| External Descriptors | Not available |
| Solubility | DMSO : 25 mg/mL (58.62 mM; ultrasonic and warming and heat to 60°C) |
|---|---|
| Molecular Weight | 426.500 g/mol |
| XLogP3 | 4.300 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 6 |
| Exact Mass | 426.168 Da |
| Monoisotopic Mass | 426.168 Da |
| Topological Polar Surface Area | 88.100 Ų |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Complexity | 835.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 2 |
| Covalently-Bonded Unit Count | 1 |
