Synonym
AMPK activator C2; C2; Compound 2; Compound-2;
IUPAC/Chemical Name
5-(5-Hydroxyl-isoxazol-3-yl)-furan-2-phosphonic acid
InChi Key
BRLJHMCTDKAUAY-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H6NO6P/c9-6-3-4(8-14-6)5-1-2-7(13-5)15(10,11)12/h1-3,9H,(H2,10,11,12)
SMILES Code
OP(C1=CC=C(C2=NOC(O)=C2)O1)(O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
231.09
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Langendorf CG, Ngoei KR, Scott JW, Ling NX, Issa SM, Gorman MA, Parker MW, Sakamoto K, Oakhill JS, Kemp BE. Structural basis of allosteric and synergistic activation of AMPK by furan-2-phosphonic derivative C2 binding. Nat Commun. 2016 Mar 8;7:10912. doi: 10.1038/ncomms10912. PubMed PMID: 26952388; PubMed Central PMCID: PMC4786773.
2: Ljubicic V, Jasmin BJ. Metformin increases peroxisome proliferator-activated receptor γ Co-activator-1α and utrophin a expression in dystrophic skeletal muscle. Muscle Nerve. 2015 Jul;52(1):139-42. doi: 10.1002/mus.24692. Epub 2015 May 14. PubMed PMID: 25908446.
3: Hunter RW, Foretz M, Bultot L, Fullerton MD, Deak M, Ross FA, Hawley SA, Shpiro N, Viollet B, Barron D, Kemp BE, Steinberg GR, Hardie DG, Sakamoto K. Mechanism of action of compound-13: an α1-selective small molecule activator of AMPK. Chem Biol. 2014 Jul 17;21(7):866-79. doi: 10.1016/j.chembiol.2014.05.014. PubMed PMID: 25036776; PubMed Central PMCID: PMC4104029.
4: Li AJ, Wang Q, Ritter S. Participation of hindbrain AMP-activated protein kinase in glucoprivic feeding. Diabetes. 2011 Feb;60(2):436-42. doi: 10.2337/db10-0352. PubMed PMID: 21270255; PubMed Central PMCID: PMC3028342.
