Terpendole E

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MedKoo CAT#: 564493

CAS#: 167427-23-8

Description: Terpendole E is an atypical L5 site inhibitor.

Chemical Structure

Terpendole E
CAS# 167427-23-8

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

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1mg USD 420
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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 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:

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.

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
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.