2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one
2-(2-AMINO-3-METHOXYPHENYL)-4H-CHROMEN-4-ONE · CS-398 · PD 98059 · PD090859 · PD 98,59 · PD 098,059 · PD 98059 NEW · PD 98059, 99+%
Identifiers & Physical Properties
| CAS No. | 167869-21-8 |
|---|---|
| Molecular formula | C16H13NO3 |
| Average molar mass | 267.28 g/mol |
| Monoisotopic mass | 267.08954328 g/mol |
| SMILES | COc1cccc(-c2cc(=O)c3ccccc3o2)c1N |
| InChIKey | QFWCYNPOPKQOKV-UHFFFAOYSA-N |
| PubChem CID | 4713 |
| ChEMBL | CHEMBL35482 |
| ChEBI | CHEBI:77954 |
| EC No. | 620-943-7 |
| DTXSID | DTXSID40168416 |
Chemical & Physical Properties
| XLogP | 2.9 |
|---|---|
| Topological polar surface area | 61.6 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 2 |
| Heavy atoms | 20 |
| Formal charge | 0 |
| Complexity | 407 |
| Melting point | 164~165℃ |
| Boiling point | 453.1±45.0 °C(Predicted) |
| Density | 1.300±0.06 g/cm3(Predicted) |
| Storage conditions | -20°C |
| Solubility | ethanol: 0.6 mg/mL |
| pKa (acidity coefficient) | 1.21±0.10(Predicted) |
| Physical state | solid |
| Color | yellow |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| InChI | InChI=1S/C16H13NO3/c1-19-14-8-4-6-11(16(14)17)15-9-12(18)10-5-2-3-7-13(10)20-15/h2-9H,17H2,1H3 |
| InChIKey | QFWCYNPOPKQOKV-UHFFFAOYSA-N |
| SMILES | C1(C2=CC=CC(OC)=C2N)OC2=CC=CC=C2C(=O)C=1 |
| CAS DataBase Reference | 167869-21-8(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | SJE1IO5E3I |
| UNSPSC Code | 12352202 |
| NACRES | NA.77 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312a-P330-P501a |
| Hazard symbols | Xn |
| Risk statements (R) | 22 |
| Safety statements (S) | 22-60-36 |
| UN transport number | UN 2811 6.1/PG 3 |
| Water hazard class (WGK) | 3 |
| Customs code | 29322090 |
| Storage class | 10 - Combustible liquids |
Safety & Regulations
| GHS classification | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Water hazard class (WGK) | 3 |
| UN transport number | UN 2811 6.1/PG 3 |
| Customs code | 29322090 |
| Risk statements (R) | 22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 22-60-36 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312a-P330-P501a |
Applications & Uses
Description
PD 98059 is a noncompetitive inhibitor of the MAPK pathway. It prevents the activation of MEK by Raf or MEK kinase (a MAP3K) with an IC50 value of 2-7 μM but does not inhibit Raf-activated MAP2K1. It inhibits Raf activation of MAP2K2 with an IC50 value of 50 μM. PD 98059 also phosphorylates and activates AMP-activated protein kinase (AMPK) in a dose-dependent manner (EC50 = 35 μM in HEK293 cells). It increases the ratios of ADP to ATP and AMP to ATP and increases phosphorylation of the AMPK target acetyl-CoA carboxylase (ACC).
Uses
PD 98059 is a selective inhibitor of MEK and blocker of MAPK.
General Description
Selective, reversible, and cell-permeable inhibitor of MAP kinase kinase (MEK) that acts by inhibiting the activation of MAP kinase and subsequent phosphorylation of MAP kinase substrates. Pretreatment of PC-12 cells with PD 98059 completely blocks the 4-fold increase in MAP kinase activity produced by nerve growth factor (NGF; IC50 = 2 μM); however, it has no effect on NGF-dependent tyrosine phosphorylation of the p140trk receptor or its substrate Shc and does not block NGF-dependent activation of PI 3-kinase. Blocks LPS-induced activation of TNF-α gene expression. Inhibits cell growth and reverses the phenotype of ras-transformed BALB3T3 mouse fibroblasts and rat kidney cells. A 5 mg/ml solution of PD 98059 (Cat. No. 513001) in anhydrous DMSO is also available.