MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 564422 | Name: Epolactaene

Description:

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

Epolactaene is a neuritogenic compound in human neuroblastoma cells which selectively inhibit the activities of mammalian DNA polymerases and human DNA topoisomerase II.

Chemical Structure

Epolactaene
Epolactaene
CAS#167782-17-4

Theoretical Analysis

MedKoo Cat#: 564422

Name: Epolactaene

CAS#: 167782-17-4

Chemical Formula: C21H27NO6

Exact Mass: 389.1838

Molecular Weight: 389.45

Elemental Analysis: C, 64.77; H, 6.99; N, 3.60; O, 24.65

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Epolactaene
IUPAC/Chemical Name
Methyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate
InChi Key
GFRNQYUCUNYIEN-ZLXMTJSISA-N
InChi Code
InChI=1S/C21H27NO6/c1-6-15(17(24)27-5)12-13(2)10-8-7-9-11-14(3)16(23)21-18(28-21)20(4,26)22-19(21)25/h6,8,10-12,18,26H,7,9H2,1-5H3,(H,22,25)/b10-8+,13-12+,14-11+,15-6+/t18-,20?,21-/m0/s1
SMILES Code
O=C(OC)C(/C=C(C)/C=C/CC/C=C(C)/C([C@@]12C(NC(C)(O)[C@]1([H])O2)=O)=O)=C/C
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 389.45 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: Kuramochi K, Sunoki T, Tsubaki K, Mizushina Y, Sakaguchi K, Sugawara F, Ikekita M, Kobayashi S. Transformation of thiols to disulfides by epolactaene and its derivatives. Bioorg Med Chem. 2011 Jul 15;19(14):4162-72. doi: 10.1016/j.bmc.2011.06.015. Epub 2011 Jun 13. PubMed PMID: 21708466. 2: Kuramochi K, Yukizawa S, Ikeda S, Sunoki T, Arai S, Matsui R, Morita A, Mizushina Y, Sakaguchi K, Sugawara F, Ikekita M, Kobayashi S. Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation. Bioorg Med Chem. 2008 May 1;16(9):5039-49. doi: 10.1016/j.bmc.2008.03.029. Epub 2008 Mar 14. PubMed PMID: 18375133. 3: Kuramochi K, Matsui R, Matsubara Y, Nakai J, Sunoki T, Arai S, Nagata S, Nagahara Y, Mizushina Y, Ikekita M, Kobayashi S. Apoptosis-inducing effect of epolactaene derivatives on BALL-1 cells. Bioorg Med Chem. 2006 Apr 1;14(7):2151-61. Epub 2005 Nov 18. PubMed PMID: 16298530. 4: Mizushina Y, Kuramochi K, Ikawa H, Kuriyama I, Shimazaki N, Takemura M, Oshige M, Yoshida H, Koiwai O, Sugawara F, Kobayashi S, Sakaguchi K. Structural analysis of epolactaene derivatives as DNA polymerase inhibitors and anti-inflammatory compounds. Int J Mol Med. 2005 May;15(5):785-93. PubMed PMID: 15806299. 5: Nagumo Y, Kakeya H, Shoji M, Hayashi Y, Dohmae N, Osada H. Epolactaene binds human Hsp60 Cys442 resulting in the inhibition of chaperone activity. Biochem J. 2005 May 1;387(Pt 3):835-40. PubMed PMID: 15603555; PubMed Central PMCID: PMC1135015. 6: Nagumo Y, Kakeya H, Yamaguchi J, Uno T, Shoji M, Hayashi Y, Osada H. Structure-activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4425-9. PubMed PMID: 15357965. 7: Hayashi Y, Kanayama J, Yamaguchi J, Shoji M. Diastereoselective total synthesis of both enantiomers of epolactaene. J Org Chem. 2002 Dec 27;67(26):9443-8. PubMed PMID: 12492351. 8: Nakai J, Kawada K, Nagata S, Kuramochi K, Uchiro H, Kobayashi S, Ikekita M. A novel lipid compound, epolactaene, induces apoptosis: its action is modulated by its side chain structure. Biochim Biophys Acta. 2002 Mar 15;1581(1-2):1-10. PubMed PMID: 11960746. 9: Mizushina Y, Kobayashi S, Kuramochi K, Nagata S, Sugawara F, Sakaguchi K. Epolactaene, a novel neuritogenic compound in human neuroblastoma cells, selectively inhibits the activities of mammalian DNA polymerases and human DNA topoisomerase II. Biochem Biophys Res Commun. 2000 Jul 5;273(2):784-8. PubMed PMID: 10873681. 10: Kakeya H, Takahashi I, Okada G, Isono K, Osada H. Epolactaene, a novel neuritogenic compound in human neuroblastoma cells, produced by a marine fungus. J Antibiot (Tokyo). 1995 Jul;48(7):733-5. PubMed PMID: 7649877.