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MedKoo Cat#: 561249 | Name: Demethoxyviridin

Description:

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

Demethoxyviridin, or DMV, is a low-nanomolar inhibitor of mammalian Ptdlns 3-kinase that binds to the catalytic subunit (p110) of the enzyme. Demethoxyviridin is also an antifungal agent structurally related to wortmannin.

Chemical Structure

Demethoxyviridin
Demethoxyviridin
CAS#56660-21-0

Theoretical Analysis

MedKoo Cat#: 561249

Name: Demethoxyviridin

CAS#: 56660-21-0

Chemical Formula: C19H14O5

Exact Mass: 322.0841

Molecular Weight: 322.32

Elemental Analysis: C, 70.80; H, 4.38; O, 24.82

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Demethoxyviridin; DMV
IUPAC/Chemical Name
(1R,11bR)-1-Hydroxy-11b-methyl-1,7,8,11b-tetrahydrocyclopenta[7,8]phenanthro[10,1-bc]furan-3,6,9(2H)-trione
InChi Key
SWJBYJJNDIXFSA-KUHUBIRLSA-N
InChi Code
InChI=1S/C19H14O5/c1-19-11-4-2-8-9(3-5-12(8)20)15(11)17(23)18-16(19)10(7-24-18)13(21)6-14(19)22/h2,4,7,14,22H,3,5-6H2,1H3/t14-,19+/m1/s1
SMILES Code
O=C1C[C@@H](O)[C@](C2=C3OC=C21)(C)C4=C(C3=O)C(CCC5=O)=C5C=C4
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 322.32 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.

Recalculate based on batch purity %
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: Kiran I, Ilhan S, Akar T, Tur L, Erol E. Synthesis and evaluation of demethoxyviridin derivatives as potential antimicrobials. Z Naturforsch C. 2005 Sep-Oct;60(9-10):686-92. PubMed PMID: 16320609. 2: Yuan H, Pupo MT, Blois J, Smith A, Weissleder R, Clardy J, Josephson L. A stabilized demethoxyviridin derivative inhibits PI3 kinase. Bioorg Med Chem Lett. 2009 Aug 1;19(15):4223-7. doi: 10.1016/j.bmcl.2009.05.105. Epub 2009 May 30. PubMed PMID: 19523825; PubMed Central PMCID: PMC2877487. 3: Giner JL, Kehbein KA, Cook JA, Smith MC, Vlahos CJ, Badwey JA. Synthesis of fluorescent derivatives of wortmannin and demethoxyviridin as probes for phosphatidylinositol 3-kinase. Bioorg Med Chem Lett. 2006 May 1;16(9):2518-21. Epub 2006 Feb 7. PubMed PMID: 16464575. 4: Zheng QC, Chen GD, Kong MZ, Li GQ, Cui JY, Li XX, Wu ZY, Guo LD, Cen YZ, Zheng YZ, Gao H. Nodulisporisteriods A and B, the first 3,4-seco-4-methyl-progesteroids from Nodulisporium sp. Steroids. 2013 Sep;78(9):896-901. doi: 10.1016/j.steroids.2013.05.007. Epub 2013 May 17. PubMed PMID: 23685090. 5: Bonser RW, Thompson NT, Randall RW, Tateson JE, Spacey GD, Hodson HF, Garland LG. Demethoxyviridin and wortmannin block phospholipase C and D activation in the human neutrophil. Br J Pharmacol. 1991 May;103(1):1237-41. PubMed PMID: 1908735; PubMed Central PMCID: PMC1908105. 6: Petritsch C, Woscholski R, Edelmann HM, Parker PJ, Ballou LM. Selective inhibition of p70 S6 kinase activation by phosphatidylinositol 3-kinase inhibitors. Eur J Biochem. 1995 Jun 1;230(2):431-8. PubMed PMID: 7607212. 7: Woscholski R, Kodaki T, McKinnon M, Waterfield MD, Parker PJ. A comparison of demethoxyviridin and wortmannin as inhibitors of phosphatidylinositol 3-kinase. FEBS Lett. 1994 Apr 4;342(2):109-14. PubMed PMID: 8143860. 8: Baumruker T, Pendl GG, Prieschl EE. Gene regulation after Fc epsilon RI stimulation in the murine mast cell line CPII. Int Arch Allergy Immunol. 1997 May-Jul;113(1-3):39-41. PubMed PMID: 9130478. 9: Pendl GG, Prieschl EE, Thumb W, Harrer NE, Auer M, Baumruker T. Effects of phosphatidylinositol-3-kinase inhibitors on degranulation and gene induction in allergically triggered mouse mast cells. Int Arch Allergy Immunol. 1997 Apr;112(4):392-9. PubMed PMID: 9104796. 10: Cross MJ, Hodgkin MN, Plumb JA, Brunton VG, Stewart A, MacAully G, Hill R, Kerr DJ, Workman P, Wakelam MJ. Inhibition of phospholipid signalling and proliferation of Swiss 3T3 cells by the wortmannin analogue demethoxyviridin. Biochim Biophys Acta. 1997 Nov 28;1362(1):29-38. PubMed PMID: 9434097. 11: Thompson NT, Bonser RW, Tateson JE, Spacey GD, Randall RW, Hodson HF, Garland LG. A quantitative investigation into the dependence of Ca2+ mobilisation on changes in inositol 1,4,5-trisphosphate levels in the stimulated neutrophil. Br J Pharmacol. 1991 Jun;103(2):1592-6. PubMed PMID: 1884113; PubMed Central PMCID: PMC1908335. 12: Cross MJ, Stewart A, Hodgkin MN, Kerr DJ, Wakelam MJ. Wortmannin and its structural analogue demethoxyviridin inhibit stimulated phospholipase A2 activity in Swiss 3T3 cells. Wortmannin is not a specific inhibitor of phosphatidylinositol 3-kinase. J Biol Chem. 1995 Oct 27;270(43):25352-5. PubMed PMID: 7592698. 13: Cengiz Ustuner M, Degirmenci I, Kiran I, Ozden H, Civi K, Ustuner D, Gunes HV. The protective effects of demethoxyviridine and 1-alpha-hydroxy-demethoxyviridine in the livers of male rats treated with diethylnitrosamine and 2-acetylaminflourene. Saudi Med J. 2008 Sep;29(9):1241-6. PubMed PMID: 18813404. 14: Kodaki T, Woscholski R, Parker PJ. V-Ras activates phosphatidylinositol 3-kinase. Biochem Soc Trans. 1995 May;23(2):195S. PubMed PMID: 7672216. 15: Torrance CJ, Agrawal V, Vogelstein B, Kinzler KW. Use of isogenic human cancer cells for high-throughput screening and drug discovery. Nat Biotechnol. 2001 Oct;19(10):940-5. PubMed PMID: 11581659.