S-4048

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 532621

CAS#: 173534-37-7

Description: S-4048 is a very potent inhibitor of glucose-6-phosphate translocase (G6P T1). S-4048 acts as a gatekeeper to transport glucose 6-phosphate into the endoplasmic reticulum and therefore plays an important role in the regulation of blood glucose levels.


Price and Availability

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S-4048 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 532621
Name: S-4048
CAS#: 173534-37-7
Chemical Formula: C32H30ClN3O7
Exact Mass: 603.1772
Molecular Weight: 604.06
Elemental Analysis: C, 63.63; H, 5.01; Cl, 5.87; N, 6.96; O, 18.54


Synonym: S-4048; S 4048; S4048.

IUPAC/Chemical Name: (1S,3R,4R,5R)-1-[[(1R,2S)-2-(4-chlorophenyl)cyclopropyl]methoxy]-3,4-dihydroxy-5-[(Z)-3-imidazo[4,5-b]pyridin-1-yl-3-phenylprop-2-enoyl]oxycyclohexane-1-carboxylic acid

InChi Key: MYXPHMOLFCUDIL-MLFVSVOESA-N

InChi Code: InChI=1S/C32H30ClN3O7/c33-22-10-8-19(9-11-22)23-13-21(23)17-42-32(31(40)41)15-26(37)29(39)27(16-32)43-28(38)14-25(20-5-2-1-3-6-20)36-18-35-30-24(36)7-4-12-34-30/h1-12,14,18,21,23,26-27,29,37,39H,13,15-17H2,(H,40,41)/b25-14-/t21-,23+,26+,27+,29+,32-/m0/s1

SMILES Code: O=C([C@]1(OC[C@H]2[C@@H](C3=CC=C(Cl)C=C3)C2)C[C@@H](O)[C@@H](O)[C@H](OC(/C=C(N4C=NC5=NC=CC=C54)/C6=CC=CC=C6)=O)C1)O


Technical Data

Appearance:
Solid powder

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).

Harmonized System Code:
293490


References

1: Grefhorst A, Schreurs M, Oosterveer MH, Cortés VA, Havinga R, Herling AW, Reijngoud DJ, Groen AK, Kuipers F. Carbohydrate-response-element-binding protein (ChREBP) and not the liver X receptor α (LXRα) mediates elevated hepatic lipogenic gene expression in a mouse model of glycogen storage disease type 1. Biochem J. 2010 Dec 1;432(2):249-54. doi: 10.1042/BJ20101225. PubMed PMID: 20854262.

2: Dubbelhuis PF, Van Sluijters DA, Blommaart EF, Gustafson LA, Van Woerkom GM, Herling AW, Burger HJ, Meijer AJ. Inhibition of autophagic proteolysis by inhibitors of phosphoinositide 3-kinase can interfere with the regulation of glycogen synthesis in isolated hepatocytes. Biochem J. 2002 Dec 15;368(Pt 3):827-33. PubMed PMID: 12371905; PubMed Central PMCID: PMC1223050.

3: Hosokawa M, Thorens B. Glucose release from GLUT2-null hepatocytes: characterization of a major and a minor pathway. Am J Physiol Endocrinol Metab. 2002 Apr;282(4):E794-801. PubMed PMID: 11882499.

4: Herling AW, Schwab D, Burger HJ, Maas J, Hammerl R, Schmidt D, Strohschein S, Hemmerle H, Schubert G, Petry S, Kramer W. Prolonged blood glucose reduction in mrp-2 deficient rats (GY/TR(-)) by the glucose-6-phosphate translocase inhibitor S 3025. Biochim Biophys Acta. 2002 Jan 15;1569(1-3):105-10. PubMed PMID: 11853963.

5: Bandsma RH, Wiegman CH, Herling AW, Burger HJ, ter Harmsel A, Meijer AJ, Romijn JA, Reijngoud DJ, Kuipers F. Acute inhibition of glucose-6-phosphate translocator activity leads to increased de novo lipogenesis and development of hepatic steatosis without affecting VLDL production in rats. Diabetes. 2001 Nov;50(11):2591-7. PubMed PMID: 11679439.

6: Gustafson LA, Neeft M, Reijngoud DJ, Kuipers F, Sauerwein HP, Romijn JA, Herling AW, Burger HJ, Meijer AJ. Fatty acid and amino acid modulation of glucose cycling in isolated rat hepatocytes. Biochem J. 2001 Sep 15;358(Pt 3):665-71. PubMed PMID: 11535127; PubMed Central PMCID: PMC1222100.

7: van Dijk TH, van der Sluijs FH, Wiegman CH, Baller JF, Gustafson LA, Burger HJ, Herling AW, Kuipers F, Meijer AJ, Reijngoud DJ. Acute inhibition of hepatic glucose-6-phosphatase does not affect gluconeogenesis but directs gluconeogenic flux toward glycogen in fasted rats. A pharmacological study with the chlorogenic acid derivative S4048. J Biol Chem. 2001 Jul 13;276(28):25727-35. Epub 2001 May 9. PubMed PMID: 11346646.

8: Burger HJ, Schubert G, Hemmerle H, Kramer W, Herling AW. Pharmacological interference with hepatic glucose production. Ann N Y Acad Sci. 1999 Nov 18;892:312-4. PubMed PMID: 10842672.

9: Herling AW, Burger H, Schubert G, Hemmerle H, Schaefer H, Kramer W. Alterations of carbohydrate and lipid intermediary metabolism during inhibition of glucose-6-phosphatase in rats. Eur J Pharmacol. 1999 Dec 10;386(1):75-82. PubMed PMID: 10611466.