Terretonin | CAS#71911-90-5 | biochemical

MedKoo Cat#: 146105 | Name: Terretonin

Description:

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

Terretonin is a synthetic compound designed to modulate serotonin receptors, particularly the 5-HT3 receptor. It has potential applications in treating gastrointestinal disorders, such as irritable bowel syndrome (IBS), as well as in managing nausea and vomiting. Its mechanism of action involves the selective binding to and inhibition of the 5-HT3 receptor, which is involved in the regulation of gut motility and vomiting reflexes.

Chemical Structure

Terretonin

CAS#71911-90-5

Theoretical Analysis

MedKoo Cat#: 146105

Name: Terretonin

CAS#: 71911-90-5

Chemical Formula: C26H32O9

Exact Mass: 488.2046

Molecular Weight: 488.53

Elemental Analysis: C, 63.92; H, 6.60; O, 29.47

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

Terretonin;

IUPAC/Chemical Name

methyl (2S,4aS,4bR,10aR,10bR,12aS)-6,10b-dihydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylene-1,4,5,8-tetraoxo-1,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-2H-naphtho[1,2-h]isochromene-2-carboxylate

InChi Key

CYHGEJACRPDZDP-RSQIKLETSA-N

InChi Code

1S/C26H32O9/c1-12-11-26(33)22(4)10-9-13(27)21(2,3)15(22)14(28)17(29)24(26,6)16-18(30)35-25(7,20(32)34-8)19(31)23(12,16)5/h16,28,33H,1,9-11H2,2-8H3/t16-,22+,23+,24-,25-,26+/m0/s1

SMILES Code

[H][C@]12C(=O)O[C@](C)(C(=O)OC)C(=O)[C@]1(C)C(=C)C[C@@]3(O)[C@]4(C)CCC(=O)C(C)(C)C4=C(O)C(=O)[C@]23C

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 488.53 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

1: Wu CJ, Cui X, Xiong B, Yang MS, Zhang YX, Liu XM. Terretonin D1, a new meroterpenoid from marine-derived Aspergillus terreus ML-44. Nat Prod Res. 2019 Aug;33(15):2262-2265. doi: 10.1080/14786419.2018.1493583. Epub 2018 Nov 3. PMID: 30394102. 2: Hamed A, Abdel-Razek AS, Omran DA, El-Metwally MM, El-Hosari DG, Frese M, Soliman HSM, Sewald N, Shaaban M. Terretonin O: a new meroterpenoid from Aspergillus terreus. Nat Prod Res. 2020 Apr;34(7):965-974. doi: 10.1080/14786419.2018.1544977. Epub 2019 Jan 3. PMID: 30602325. 3: Mohamed GA, Ibrahim SRM, El-Agamy DS, Elsaed WM, Sirwi A, Asfour HZ, Koshak AE, Elhady SS. Terretonin as a New Protective Agent against Sepsis-Induced Acute Lung Injury: Impact on SIRT1/Nrf2/NF-κBp65/NLRP3 Signaling. Biology (Basel). 2021 Nov 22;10(11):1219. doi: 10.3390/biology10111219. PMID: 34827212; PMCID: PMC8614783. 4: Fukuda T, Kurihara Y, Kanamoto A, Tomoda H. Terretonin G, a new sesterterpenoid antibiotic from marine-derived Aspergillus sp. OPMF00272. J Antibiot (Tokyo). 2014 Aug;67(8):593-5. doi: 10.1038/ja.2014.46. Epub 2014 May 7. PMID: 24802208. 5: Matsuda Y, Awakawa T, Itoh T, Wakimoto T, Kushiro T, Fujii I, Ebizuka Y, Abe I. Terretonin biosynthesis requires methylation as essential step for cyclization. Chembiochem. 2012 Aug 13;13(12):1738-41. doi: 10.1002/cbic.201200369. Epub 2012 Jul 10. PMID: 22782788. 6: Hamed A, Abdel-Razek AS, Frese M, Stammler HG, El-Haddad AF, Ibrahim TMA, Sewald N, Shaaban M. Terretonin N: A New Meroterpenoid from Nocardiopsis sp. Molecules. 2018 Jan 31;23(2):299. doi: 10.3390/molecules23020299. PMID: 29385078; PMCID: PMC6017310. 7: Ghfar AA, El-Metwally MM, Shaaban M, Gabr SA, Gabr NS, Diab MSM, Aqel A, Habila MA, Al-Qahtani WH, Alfaifi MY, Elbehairi SEI, AlJumah BA. Production of Terretonin N and Butyrolactone I by Thermophilic Aspergillus terreus TM8 Promoted Apoptosis and Cell Death in Human Prostate and Ovarian Cancer Cells. Molecules. 2021 May 10;26(9):2816. doi: 10.3390/molecules26092816. PMID: 34068647; PMCID: PMC8126039. 8: Shaaban M, El-Metwally MM, Abdel-Razek AA, Laatsch H. Terretonin M: A new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins. Nat Prod Res. 2018 Oct;32(20):2437-2446. doi: 10.1080/14786419.2017.1419230. Epub 2017 Dec 27. PMID: 29281919. 9: Xu G, Elkin M, Tantillo DJ, Newhouse TR, Maimone TJ. Traversing Biosynthetic Carbocation Landscapes in the Total Synthesis of Andrastin and Terretonin Meroterpenes. Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12498-12502. doi: 10.1002/anie.201705654. Epub 2017 Aug 30. PMID: 28799296; PMCID: PMC5697905. 10: Guo CJ, Knox BP, Chiang YM, Lo HC, Sanchez JF, Lee KH, Oakley BR, Bruno KS, Wang CC. Molecular genetic characterization of a cluster in A. terreus for biosynthesis of the meroterpenoid terretonin. Org Lett. 2012 Nov 16;14(22):5684-7. doi: 10.1021/ol302682z. Epub 2012 Nov 1. PMID: 23116177; PMCID: PMC3538129. 11: Matsuda Y, Iwabuchi T, Wakimoto T, Awakawa T, Abe I. Uncovering the unusual D-ring construction in terretonin biosynthesis by collaboration of a multifunctional cytochrome P450 and a unique isomerase. J Am Chem Soc. 2015 Mar 11;137(9):3393-401. doi: 10.1021/jacs.5b00570. Epub 2015 Feb 25. PMID: 25671343. 12: Elkhayat ES, Ibrahim SR, Mohamed GA, Ross SA. Terrenolide S, a new antileishmanial butenolide from the endophytic fungus Aspergillus terreus. Nat Prod Res. 2016;30(7):814-20. doi: 10.1080/14786419.2015.1072711. Epub 2015 Aug 24. PMID: 26299734. 13: Feng W, Chen C, Mo S, Qi C, Gong J, Li XN, Zhou Q, Zhou Y, Li D, Lai Y, Zhu H, Wang J, Zhang Y. Highly oxygenated meroterpenoids from the Antarctic fungus Aspergillus terreus. Phytochemistry. 2019 Aug;164:184-191. doi: 10.1016/j.phytochem.2019.05.015. Epub 2019 May 31. PMID: 31158603. 14: Mori T, Abe I. Functional analysis of a fungal P450 enzyme. Methods Enzymol. 2023;693:171-190. doi: 10.1016/bs.mie.2023.09.003. Epub 2023 Oct 13. PMID: 37977730. 15: Fang ST, Liu XH, Yan BF, Miao FP, Yin XL, Li WZ, Ji NY. Terpenoids from the Marine-Derived Fungus Aspergillus sp. RR-YLW-12, Associated with the Red Alga Rhodomela confervoides. J Nat Prod. 2021 Jun 25;84(6):1763-1771. doi: 10.1021/acs.jnatprod.1c00021. Epub 2021 May 25. PMID: 34033718. 16: Yin Y, Cai M, Zhou X, Li Z, Zhang Y. Polyketides in Aspergillus terreus: biosynthesis pathway discovery and application. Appl Microbiol Biotechnol. 2016 Sep;100(18):7787-98. doi: 10.1007/s00253-016-7733-z. Epub 2016 Jul 26. PMID: 27455860. 17: Shen X, Thach DQ, Ting CP, Maimone TJ. Annulative Methods in the Synthesis of Complex Meroterpene Natural Products. Acc Chem Res. 2021 Feb 2;54(3):583-594. doi: 10.1021/acs.accounts.0c00781. Epub 2021 Jan 15. PMID: 33448794. 18: Du X, Li H, Qi J, Chen C, Lu Y, Wang Y. Genome mining of secondary metabolites from a marine-derived Aspergillus terreus B12. Arch Microbiol. 2021 Nov;203(9):5621-5633. doi: 10.1007/s00203-021-02548-4. Epub 2021 Aug 30. PMID: 34459930. 19: Wu ZJ, Fang DM, Han D, Li GY, Chen XZ, Qi HY, Zhang GL. Analysis of sesterterpenoids from Aspergillus terreus using ESI-QTOF and ESI-IT. Phytochem Anal. 2010 Jul-Aug;21(4):374-83. doi: 10.1002/pca.1209. PMID: 20310057. 20: Tang Y, Li Y, Zhao M, Ruan Q, Liu Y, Li C, Zhao Z, Cui H. Furanasperterpenes A and B, two meroterpenoids with a novel 6/6/6/6/5 ring system from the marine- derived fungus Aspergillus terreus GZU-31-1. Bioorg Chem. 2020 Jul;100:103968. doi: 10.1016/j.bioorg.2020.103968. Epub 2020 May 22. PMID: 32470761.