MedKoo Cat#: 584908 | Name: Ovalicin

Description:

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

Ovalicin is a sesquiterpene isolated from culture filtrate of fungus Pseudorotium ovalis and shows antitumor activity.

Chemical Structure

Ovalicin
Ovalicin
CAS#19683-98-8

Theoretical Analysis

MedKoo Cat#: 584908

Name: Ovalicin

CAS#: 19683-98-8

Chemical Formula: C16H24O5

Exact Mass: 296.1624

Molecular Weight: 296.36

Elemental Analysis: C, 64.84; H, 8.16; O, 26.99

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
Ovalicin; SL-1846; (-)-Ovalicin; Graphinone
IUPAC/Chemical Name
1-Oxaspiro(2,5)octan-6-one, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-4-hydroxy-5-methoxy-, (1S,2R,3S,4R,5S)-(-)-
InChi Key
NESRXFGQJARQNM-OWYFMNJBSA-N
InChi Code
InChI=1S/C16H24O5/c1-10(2)5-6-12-14(3,21-12)16(18)13(19-4)11(17)7-8-15(16)9-20-15/h5,12-13,18H,6-9H2,1-4H3/t12-,13-,14+,15+,16+/m1/s1
SMILES Code
O=C(CC1)[C@@H](OC)[C@](O)([C@@](C)(O2)[C@H]2C/C=C(C)\C)[C@]31CO3
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
>3 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 296.36 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: Addlagatta A, Matthews BW. Structure of the angiogenesis inhibitor ovalicin bound to its noncognate target, human Type 1 methionine aminopeptidase. Protein Sci. 2006 Aug;15(8):1842-8. Epub 2006 Jul 5. PubMed PMID: 16823043; PubMed Central PMCID: PMC2242583. 2: Sorres J, Nirma C, Eparvier V, Stien D. Pseudallicins A-D: Four Complex Ovalicin Derivatives from Pseudallescheria boydii SNB-CN85. Org Lett. 2017 Aug 4;19(15):3978-3981. doi: 10.1021/acs.orglett.7b01671. Epub 2017 Jul 14. PubMed PMID: 28708403. 3: Brdlik CM, Crews CM. A single amino acid residue defines the difference in ovalicin sensitivity between type I and II methionine aminopeptidases. J Biol Chem. 2004 Mar 5;279(10):9475-80. Epub 2003 Dec 15. PubMed PMID: 14676204; PubMed Central PMCID: PMC2556556. 4: Hua DH, Zhao H, Battina SK, Lou K, Jimenez AL, Desper J, Perchellet EM, Perchellet JP, Chiang PK. Total syntheses of (+/-)-ovalicin, C4(S *)-isomer, and its C5-analogs and anti-trypanosomal activities. Bioorg Med Chem. 2008 May 1;16(9):5232-46. doi: 10.1016/j.bmc.2008.03.009. Epub 2008 Mar 6. PubMed PMID: 18356059; PubMed Central PMCID: PMC2453514. 5: Didier PJ, Phillips JN, Kuebler DJ, Nasr M, Brindley PJ, Stovall ME, Bowers LC, Didier ES. Antimicrosporidial activities of fumagillin, TNP-470, ovalicin, and ovalicin derivatives in vitro and in vivo. Antimicrob Agents Chemother. 2006 Jun;50(6):2146-55. PubMed PMID: 16723577; PubMed Central PMCID: PMC1479127. 6: Yoon CS, Nam SH, Jeon JY, Lee HS, Lee ML, Son HU, Lee SH. Ovalicin ameliorates compound 48/80-induced atopic dermatitis-related symptoms. Biol Pharm Bull. 2011;34(12):1881-4. PubMed PMID: 22130246. 7: Turk BE, Su Z, Liu JO. Synthetic analogues of TNP-470 and ovalicin reveal a common molecular basis for inhibition of angiogenesis and immunosuppression. Bioorg Med Chem. 1998 Aug;6(8):1163-9. PubMed PMID: 9784858. 8: Yamaguchi J, Hayashi Y. Syntheses of fumagillin and ovalicin. Chemistry. 2010 Apr 6;16(13):3884-901. doi: 10.1002/chem.200902433. PubMed PMID: 20209516. 9: Griffith EC, Su Z, Turk BE, Chen S, Chang YH, Wu Z, Biemann K, Liu JO. Methionine aminopeptidase (type 2) is the common target for angiogenesis inhibitors AGM-1470 and ovalicin. Chem Biol. 1997 Jun;4(6):461-71. PubMed PMID: 9224570. 10: Mekapati SB, Hansch C. QSAR of the inhibition of angiogenesis by TNP-470 and ovalicin analogues: another example of an allosteric interaction. Bioorg Med Chem. 2001 Dec;9(12):3225-30. PubMed PMID: 11711298. 11: Zimmermann WA, Hartmann GR. On the mode of action of the immunosuppressive sesquiterpene ovalicin. Eur J Biochem. 1981 Aug;118(1):143-50. PubMed PMID: 6169523. 12: Griffith EC, Su Z, Niwayama S, Ramsay CA, Chang YH, Liu JO. Molecular recognition of angiogenesis inhibitors fumagillin and ovalicin by methionine aminopeptidase 2. Proc Natl Acad Sci U S A. 1998 Dec 22;95(26):15183-8. PubMed PMID: 9860943; PubMed Central PMCID: PMC28017. 13: Pillalamarri V, Arya T, Haque N, Bala SC, Marapaka AK, Addlagatta A. Discovery of natural product ovalicin sensitive type 1 methionine aminopeptidases: molecular and structural basis. Biochem J. 2019 Mar 22;476(6):991-1003. doi: 10.1042/BCJ20180874. PubMed PMID: 30837307. 14: Hartmann GR, Richter H, Weiner EM, Zimmermann W. On the mechanism of action of the cytostatic drug anguidine and of the immunosuppressive agent ovalicin, two sesquiterpenes from fungi. Planta Med. 1978 Nov;34(3):231-52. Review. PubMed PMID: 360256. 15: Sakamoto KM, Kim KB, Kumagai A, Mercurio F, Crews CM, Deshaies RJ. Protacs: chimeric molecules that target proteins to the Skp1-Cullin-F box complex for ubiquitination and degradation. Proc Natl Acad Sci U S A. 2001 Jul 17;98(15):8554-9. Epub 2001 Jul 3. PubMed PMID: 11438690; PubMed Central PMCID: PMC37474. 16: Ehlers T, Furness S, Robinson TP, Zhong HA, Goldsmith D, Aribser J, Bowen JP. Methionine AminoPeptidase Type-2 Inhibitors Targeting Angiogenesis. Curr Top Med Chem. 2016;16(13):1478-88. Review. PubMed PMID: 26369821. 17: Addlagatta A, Hu X, Liu JO, Matthews BW. Structural basis for the functional differences between type I and type II human methionine aminopeptidases. Biochemistry. 2005 Nov 15;44(45):14741-9. PubMed PMID: 16274222. 18: Bollinger P, Sigg HP, Weber HP. [Structure of ovalicin]. Helv Chim Acta. 1973;56(3):819-30. German. PubMed PMID: 4733352. 19: Borel JF, Lazáry S, Stähelin H. Immunosuppressive effects of ovalicin-semicarbazone. Agents Actions. 1974 Dec;4(5):357-63. PubMed PMID: 4618722. 20: Arrenbrecht S, Lazàry S. Effect of the immunosuppressive agent ovalicin on the kinetics of antibody formation. Agents Actions. 1970 Dec;1(5):221-6. PubMed PMID: 5535372.