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MedKoo Cat#: 564493 | Name: Terpendole E
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Description:

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

Terpendole E is an atypical L5 site inhibitor.

Chemical Structure

Terpendole E
Terpendole E
CAS#167427-23-8

Theoretical Analysis

MedKoo Cat#: 564493

Name: Terpendole E

CAS#: 167427-23-8

Chemical Formula: C28H39NO3

Exact Mass: 437.2930

Molecular Weight: 437.62

Elemental Analysis: C, 76.85; H, 8.98; N, 3.20; O, 10.97

Price and Availability

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1mg USD 420.00
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Related CAS #
No Data
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

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
1: Vassiliadis S, Reddy P, Hemsworth J, Spangenberg GC, Guthridge KM, Rochfort SJ. Quantitation and Distribution of Epichloë-Derived Alkaloids in Perennial Ryegrass Tissues. Metabolites. 2023 Jan 30;13(2):205. doi: 10.3390/metabo13020205. PMID: 36837825; PMCID: PMC9966479. 2: Kassam R, Yadav J, Chawla G, Kundu A, Hada A, Jaiswal N, Bollinedi H, Kamil D, Devi P, Rao U. Identification, Characterization, and Evaluation of Nematophagous Fungal Species of Arthrobotrys and Tolypocladium for the Management of Meloidogyne incognita. Front Microbiol. 2021 Dec 10;12:790223. doi: 10.3389/fmicb.2021.790223. PMID: 34956156; PMCID: PMC8702965. 3: Fernando K, Reddy P, Vassiliadis S, Spangenberg GC, Rochfort SJ, Guthridge KM. The Known Antimammalian and Insecticidal Alkaloids Are Not Responsible for the Antifungal Activity of Epichloë Endophytes. Plants (Basel). 2021 Nov 17;10(11):2486. doi: 10.3390/plants10112486. PMID: 34834850; PMCID: PMC8624124. 4: Bauer JI, Gross M, Cramer B, Wegner S, Hausmann H, Hamscher G, Usleber E. Detection of the tremorgenic mycotoxin paxilline and its desoxy analog in ergot of rye and barley: a new class of mycotoxins added to an old problem. Anal Bioanal Chem. 2017 Aug;409(21):5101-5112. doi: 10.1007/s00216-017-0455-y. Epub 2017 Jul 4. PMID: 28674820. 5: Lee ST, Gardner DR, Cook D. Identification of Indole Diterpenes in Ipomoea asarifolia and Ipomoea muelleri, Plants Tremorgenic to Livestock. J Agric Food Chem. 2017 Jul 5;65(26):5266-5277. doi: 10.1021/acs.jafc.7b01834. Epub 2017 Jun 20. Erratum in: J Agric Food Chem. 2017 Aug 2;65(30):6342. doi: 10.1021/acs.jafc.7b03237. PMID: 28571312. 6: Sheff JG, Farshidfar F, Bathe OF, Kopciuk K, Gentile F, Tuszynski J, Barakat K, Schriemer DC. Novel Allosteric Pathway of Eg5 Regulation Identified through Multivariate Statistical Analysis of Hydrogen-Exchange Mass Spectrometry (HX-MS) Ligand Screening Data. Mol Cell Proteomics. 2017 Mar;16(3):428-437. doi: 10.1074/mcp.M116.064246. Epub 2017 Jan 5. PMID: 28062800; PMCID: PMC5341003. 7: Motoyama T, Osada H. Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism. Bioorg Med Chem Lett. 2016 Dec 15;26(24):5843-5850. doi: 10.1016/j.bmcl.2016.11.013. Epub 2016 Nov 9. PMID: 27865702. 8: 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. PMID: 25184606. 9: 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. PMID: 24913406; PMCID: PMC4207197. 10: 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. PMID: 24648249. 11: 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. PMID: 23261604. 12: Oishi S, Watanabe T, Sawada J, Asai A, Ohno H, Fujii N. Kinesin spindle protein (KSP) inhibitors with 2,3-fused indole scaffolds. J Med Chem. 2010 Jul 8;53(13):5054-8. doi: 10.1021/jm100476d. PMID: 20521839. 13: 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. PMID: 20387880. 14: Jiang C, Chen Y, Wang X, You Q. Docking studies on kinesin spindle protein inhibitors: an important cooperative 'minor binding pocket' which increases the binding affinity significantly. J Mol Model. 2007 Sep;13(9):987-92. doi: 10.1007/s00894-007-0219-2. Epub 2007 Jun 23. PMID: 17588180. 15: Osada H. Development and application of bioprobes for Mammalian cell cycle analyses. Curr Med Chem. 2003 May;10(9):727-32. doi: 10.2174/0929867033457836. PMID: 12678775. 16: 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. doi: 10.1016/s1074-5521(03)00020-6. PMID: 12618185.

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