MedKoo Biosciences

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

MedKoo CAT#: 564493

CAS#: 167427-23-8

Description: Terpendole E is an atypical L5 site inhibitor.

Chemical Structure

Terpendole E

CAS# 167427-23-8

Instruction

Theoretical Analysis

MedKoo Cat#: 564493
Name: Terpendole E
CAS#: 167427-23-8
Chemical Formula: C28H39NO3
Exact Mass: 437.29
Molecular Weight: 437.620
Elemental Analysis: C, 76.85; H, 8.98; N, 3.20; O, 10.97

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 420
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: TerpendoleE; Terpendole-E; Terpendole E

IUPAC/Chemical Name: (2S,4R,4aR,4bR,6aS,12bS,12cS,14aS)-2-(2-Hydroxypropan-2-yl)-4a,12b,12c-trimethyl-3,4,4a,4b,5,6,6a,7,12,12b,12c,13,14,14a-tetradecahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-4-ol

InChi Key: SVYIMXYKHRBHSG-KYYKPQATSA-N

InChi Code: InChI=1S/C28H39NO3/c1-25(2,31)23-15-21(30)27(4)20-11-10-16-14-18-17-8-6-7-9-19(17)29-24(18)28(16,5)26(20,3)13-12-22(27)32-23/h6-9,16,20-23,29-31H,10-15H2,1-5H3/t16-,20+,21+,22-,23-,26-,27+,28+/m0/s1

SMILES Code: CC(O)(C)[C@@H]1C[C@@H](O)[C@@]2(C)[C@@H]3CC[C@H]([C@@]4(C)[C@@]3(C)CC[C@@H]2O1)CC5=C4NC6=C5C=CC=C6

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 437.62 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Teranishi T, Murokawa T, Enomoto M, Kuwahara S. Synthesis of (±)-terpendole E. Biosci Biotechnol Biochem. 2015;79(1):11-5. doi: 10.1080/09168451.2014.955455. Epub 2014 Sep 3. PubMed PMID: 25184606.

2: Hongo Y, Nakamura T, Takahashi S, Motoyama T, Hayashi T, Hirota H, Osada H, Koshino H. Detection of oxygen addition peaks for terpendole E and related indole-diterpene alkaloids in a positive-mode ESI-MS. J Mass Spectrom. 2014 Jun;49(6):537-42. doi: 10.1002/jms.3360. PubMed PMID: 24913406; PubMed Central PMCID: PMC4207197.

3: Tarui Y, Chinen T, Nagumo Y, Motoyama T, Hayashi T, Hirota H, Muroi M, Ishii Y, Kondo H, Osada H, Usui T. Terpendole E and its derivative inhibit STLC- and GSK-1-resistant Eg5. Chembiochem. 2014 May 5;15(7):934-8. doi: 10.1002/cbic.201300808. Epub 2014 Mar 19. PubMed PMID: 24648249.

4: Motoyama T, Hayashi T, Hirota H, Ueki M, Osada H. Terpendole E, a kinesin Eg5 inhibitor, is a key biosynthetic intermediate of indole-diterpenes in the producing fungus Chaunopycnis alba. Chem Biol. 2012 Dec 21;19(12):1611-9. doi: 10.1016/j.chembiol.2012.10.010. PubMed PMID: 23261604.

5: Churruca F, Fousteris M, Ishikawa Y, Rekowski Mv, Hounsou C, Surrey T, Giannis A. A novel approach to indoloditerpenes by Nazarov photocyclization: synthesis and biological investigations of terpendole E analogues. Org Lett. 2010 May 7;12(9):2096-9. doi: 10.1021/ol100579w. PubMed PMID: 20387880.

6: Nakazawa J, Yajima J, Usui T, Ueki M, Takatsuki A, Imoto M, Toyoshima YY, Osada H. A novel action of terpendole E on the motor activity of mitotic Kinesin Eg5. Chem Biol. 2003 Feb;10(2):131-7. PubMed PMID: 12618185.

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Terpendole E featured