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Pyromeconic acid

CAS# 496-63-9

Pyromeconic acid

2D Structure

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3D structure

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Pyromeconic acid

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Chemical Properties of Pyromeconic acid

Cas No. 496-63-9 SDF Download SDF
PubChem ID 68129 Appearance Powder
Formula C5H4O3 M.Wt 112.08
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-hydroxypyran-4-one
SMILES C1=COC=C(C1=O)O
Standard InChIKey VEYIMQVTPXPUHA-UHFFFAOYSA-N
Standard InChI InChI=1S/C5H4O3/c6-4-1-2-8-3-5(4)7/h1-3,7H
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.

Source of Pyromeconic acid

The herbs of Erigeron annuus

Biological Activity of Pyromeconic acid

DescriptionPyromeconic acid and derivatives thereof are potent inhibitors of endonuclease, it shows siderophile activity.
TargetsAntifection

Protocol of Pyromeconic acid

Kinase Assay

Fragment-Based Identification of Influenza Endonuclease Inhibitors.[Pubmed: 27291165 ]

J Med Chem. 2016 Jul 14;59(13):6444-54.

The influenza virus is responsible for millions of cases of severe illness annually. Yearly variance in the effectiveness of vaccination, coupled with emerging drug resistance, necessitates the development of new drugs to treat influenza infections. One attractive target is the RNA-dependent RNA polymerase PA subunit.
METHODS AND RESULTS:
Herein we report the development of inhibitors of influenza PA endonuclease derived from lead compounds identified from a metal-binding pharmacophore (MBP) library screen. Pyromeconic acid and derivatives thereof were found to be potent inhibitors of endonuclease. Guided by modeling and previously reported structural data, several sublibraries of molecules were elaborated from the MBP hits. Structure-activity relationships were established, and more potent molecules were designed and synthesized using fragment growth and fragment merging strategies.
CONCLUSIONS:
This approach ultimately resulted in the development of a lead compound with an IC50 value of 14 nM, which displayed an EC50 value of 2.1 μM against H1N1 influenza virus in MDCK cells.

Structure Identification
Biosci Biotechnol Biochem. 1995 May;59(5):886-90.

Pyromeconic acid and its glucosidic derivatives from leaves of Erigeron annuus, and the siderophile activity of pyromeconic acid.[Pubmed: 7787303]

3'-O-Caffeylerigeroside (Pyromeconic acid 3-O-beta-D-glucoside 3'-O-caffeyl ester) was obtained from the leaves of Erigeron annuus as a new Pyromeconic acid derivative, and its structure was elucidated. Together with the gamma-pyrone derivative, Pyromeconic acid (3-hydroxy-4H-pyran-4-one) and its beta-glucoside (erigeroside) were also isolated from the aerial parts of E. annuus. The siderophile activity of Pyromeconic acid was also studied.

Pyromeconic acid Dilution Calculator

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Pyromeconic acid Molarity Calculator

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Preparing Stock Solutions of Pyromeconic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 8.9222 mL 44.611 mL 89.222 mL 178.444 mL 223.055 mL
5 mM 1.7844 mL 8.9222 mL 17.8444 mL 35.6888 mL 44.611 mL
10 mM 0.8922 mL 4.4611 mL 8.9222 mL 17.8444 mL 22.3055 mL
50 mM 0.1784 mL 0.8922 mL 1.7844 mL 3.5689 mL 4.4611 mL
100 mM 0.0892 mL 0.4461 mL 0.8922 mL 1.7844 mL 2.2305 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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References on Pyromeconic acid

Fragment-Based Identification of Influenza Endonuclease Inhibitors.[Pubmed:27291165]

J Med Chem. 2016 Jul 14;59(13):6444-54.

The influenza virus is responsible for millions of cases of severe illness annually. Yearly variance in the effectiveness of vaccination, coupled with emerging drug resistance, necessitates the development of new drugs to treat influenza infections. One attractive target is the RNA-dependent RNA polymerase PA subunit. Herein we report the development of inhibitors of influenza PA endonuclease derived from lead compounds identified from a metal-binding pharmacophore (MBP) library screen. Pyromeconic acid and derivatives thereof were found to be potent inhibitors of endonuclease. Guided by modeling and previously reported structural data, several sublibraries of molecules were elaborated from the MBP hits. Structure-activity relationships were established, and more potent molecules were designed and synthesized using fragment growth and fragment merging strategies. This approach ultimately resulted in the development of a lead compound with an IC50 value of 14 nM, which displayed an EC50 value of 2.1 muM against H1N1 influenza virus in MDCK cells.

Pyromeconic acid and its glucosidic derivatives from leaves of Erigeron annuus, and the siderophile activity of pyromeconic acid.[Pubmed:7787303]

Biosci Biotechnol Biochem. 1995 May;59(5):886-90.

3'-O-Caffeylerigeroside (Pyromeconic acid 3-O-beta-D-glucoside 3'-O-caffeyl ester) was obtained from the leaves of Erigeron annuus as a new Pyromeconic acid derivative, and its structure was elucidated. Together with the gamma-pyrone derivative, Pyromeconic acid (3-hydroxy-4H-pyran-4-one) and its beta-glucoside (erigeroside) were also isolated from the aerial parts of E. annuus. The siderophile activity of Pyromeconic acid was also studied.

Three pyrone glucosidic derivatives from Conyza albida.[Pubmed:12143010]

Planta Med. 2002 Jul;68(7):664-6.

Three new pyrone glucosidic derivatives, together with the known Pyromeconic acid glucoside, three acytelenes and two eudesmanes, were obtained from the aerial parts of Conyza albida. The structures were elucidated by high field NMR spectroscopy.

[Isolation and structure of 6'-O-caffeylerigeroside from Erigeron multiradiatus].[Pubmed:12016944]

Yao Xue Xue Bao. 1998 Nov;33(11):836-8.

The plant, Erigeron multiradiatus (Wall.) Benth(Family: Compositae), is a perennial herb distributed abundantly in the mountainous area of the southwestern part in China. It is used in folk medicine for the treatment of common cold, panting cough, rheumatic, enteritis and toothache. In this paper, we report a new glycoside named as 6'-O-caffeylerigeroside isolated from Erigeron Multiradiatus (Family: Compositae) together with four known compounds. The known compounds were identified as Pyromeconic acid(I), scopoletin(II), 4-hydroxybenzoic acid(III) and vanillic acid(IV). The structure of 6'-O-caffeylerigeroside was elucidated as gamma-pyrone-3-O-[6"-(3',4'-dihydroxy-cinnamoyl)]-beta-D-glucoside(V) on the basis of chemical evidence and spectral data.

Two new glycosides from Vitex negundo.[Pubmed:23356826]

Nat Prod Res. 2013 Oct;27(20):1837-41.

Two new glycosides, 2-methyl Pyromeconic acid 3-O-beta-D-glucopyranoside-6'-(O-4''-hydroxybenzoate) (1), 6'-O-p-hydroxybenzoyl-gardoside (2) and four known iridoid glycosides (3-6) were isolated from the whole plant of Vitex negundo. Their structures were elucidated on the basis of spectroscopic methods including HR-ESI-MS, 1D and 2D NMR.

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