Ternatin | CAS#148619-41-4 | Cyclic heptapeptide

MedKoo Cat#: 112150 | Name: Ternatin

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Description:

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

Ternatin is a cyclic heptapeptide shown to have cytotoxic and anti-adipogenic effects in vitro. Ternatin-4 is seen to act as an eEF1A inhibitor.

Chemical Structure

Ternatin

CAS#148619-41-4

Theoretical Analysis

MedKoo Cat#: 112150

Name: Ternatin

CAS#: 148619-41-4

Chemical Formula: C37H67N7O8

Exact Mass: 737.5051

Molecular Weight: 737.98

Elemental Analysis: C, 60.22; H, 9.15; N, 13.29; O, 17.34

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 750.00	2 Weeks
5mg	USD 1,500.00	2 Weeks

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Related CAS #

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Synonym

Ternatin; 1,4,7,10,13,16,19-Heptaazacycloheneicosane; (-)-Ternatin

IUPAC/Chemical Name

(3S,6S,9S,12S,15R,18R,21R)-15-((S)-sec-butyl)-18-((R)-1-hydroxy-2-methylpropyl)-6,9-diisobutyl-1,3,4,10,12,13,21-heptamethyl-1,4,7,10,13,16,19-heptaazacyclohenicosane-2,5,8,11,14,17,20-heptaone

InChi Key

ZMFVAIFXJWEOMH-PTPSPKLBSA-N

InChi Code

InChI=1S/C37H67N7O8/c1-16-22(8)28-37(52)43(14)25(11)35(50)44(15)27(18-20(4)5)32(47)38-26(17-19(2)3)36(51)42(13)24(10)34(49)41(12)23(9)31(46)40-29(33(48)39-28)30(45)21(6)7/h19-30,45H,16-18H2,1-15H3,(H,38,47)(H,39,48)(H,40,46)/t22-,23+,24-,25-,26-,27-,28+,29+,30+/m0/s1

SMILES Code

O=C([C@@H](N(C([C@@H](N(C)C([C@]([H])(NC([C@@]([H])([C@H](O)C(C)C)NC([C@H](N(C1=O)C)C)=O)=O)[C@@H](C)CC)=O)C)=O)C)CC(C)C)N[C@H](C(N([C@H]1C)C)=O)CC(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

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 737.98 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

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J Biomol Struct Dyn. 2023 Nov;41(19):9797-9807. doi: 10.1080/07391102.2022.2146752. Epub 2022 Nov 15. PMID: 36379684. 4: Juette MF, Carelli JD, Rundlet EJ, Brown A, Shao S, Ferguson A, Wasserman MR, Holm M, Taunton J, Blanchard SC. Didemnin B and ternatin-4 differentially inhibit conformational changes in eEF1A required for aminoacyl-tRNA accommodation into mammalian ribosomes. Elife. 2022 Oct 20;11:e81608. doi: 10.7554/eLife.81608. PMID: 36264623; PMCID: PMC9584604. 5: Wang HY, Yang H, Holm M, Tom H, Oltion K, Al-Khdhairawi AAQ, Weber JF, Blanchard SC, Ruggero D, Taunton J. Synthesis and single-molecule imaging reveal stereospecific enhancement of binding kinetics by the antitumour eEF1A antagonist SR-A3. Nat Chem. 2022 Dec;14(12):1443-1450. doi: 10.1038/s41557-022-01039-3. Epub 2022 Sep 19. PMID: 36123449; PMCID: PMC10018702. 6: Jeyaraj EJ, Lim YY, Choo WS. Antioxidant, cytotoxic, and antibacterial activities of Clitoria ternatea flower extracts and anthocyanin-rich fraction. Sci Rep. 2022 Sep 1;12(1):14890. doi: 10.1038/s41598-022-19146-z. PMID: 36050436; PMCID: PMC9436976. 7: Yang X, Pan X, Li M, Zeng Z, Guo Y, Chen P, Liang X, Chen P, Liu G. Interaction between Cervical Microbiota and Host Gene Regulation in Caesarean Section Scar Diverticulum. Microbiol Spectr. 2022 Aug 31;10(4):e0167622. doi: 10.1128/spectrum.01676-22. Epub 2022 Jul 28. PMID: 35900092; PMCID: PMC9430964. 8: Vidana Gamage GC, Lim YY, Choo WS. Anthocyanins From Clitoria ternatea Flower: Biosynthesis, Extraction, Stability, Antioxidant Activity, and Applications. Front Plant Sci. 2021 Dec 17;12:792303. doi: 10.3389/fpls.2021.792303. PMID: 34975979; PMCID: PMC8718764. 9: Fu X, Wu Q, Wang J, Chen Y, Zhu G, Zhu Z. Spectral Characteristic, Storage Stability and Antioxidant Properties of Anthocyanin Extracts from Flowers of Butterfly Pea (Clitoria ternatea L.). Molecules. 2021 Nov 19;26(22):7000. doi: 10.3390/molecules26227000. PMID: 34834097; PMCID: PMC8622631. 10: Nugraha AP, Rahmadhani D, Puspitaningrum MS, Rizqianti Y, Kharisma VD, Ernawati DS. Molecular docking of anthocyanins and ternatin in Clitoria ternatea as coronavirus disease oral manifestation therapy. J Adv Pharm Technol Res. 2021 Oct-Dec;12(4):362-367. doi: 10.4103/japtr.japtr_126_21. Epub 2021 Oct 20. PMID: 34820310; PMCID: PMC8588916. 11: Kim HJ, Li XJ, Kim DC, Kim TK, Sohn JH, Kwon H, Lee D, Kim YC, Yim JH, Oh H. PTP1B Inhibitory Secondary Metabolites from an Antarctic Fungal Strain Acremonium sp. SF-7394. Molecules. 2021 Sep 10;26(18):5505. doi: 10.3390/molecules26185505. PMID: 34576982; PMCID: PMC8468024. 12: Carvalho KR, Souza ASQ, Alves Filho EG, Silva LMA, Silva EO, A Pereira RC, Zocolo GJ, de Brito ES, Silveira ER, Canuto KM. NIR and 1H qNMR methods coupled to chemometrics discriminate the chemotypes of the gastroprotective herb Egletes viscosa. Food Res Int. 2020 Dec;138(Pt A):109759. doi: 10.1016/j.foodres.2020.109759. Epub 2020 Oct 2. PMID: 33292941. 13: Escher GB, Wen M, Zhang L, Rosso ND, Granato D. Phenolic composition by UHPLC-Q-TOF-MS/MS and stability of anthocyanins from Clitoria ternatea L. (butterfly pea) blue petals. Food Chem. 2020 Nov 30;331:127341. doi: 10.1016/j.foodchem.2020.127341. Epub 2020 Jun 15. PMID: 32569972. 14: Rodrigues Carvalho K, Julião Zocolo G, Alves Pereira RC, Chaves Custódio Martins FI, Vasconcelos Ribeiro PR, Sousa de Brito E, Rocha Silveira E, Marques Canuto K. Development of a UPLC-ESI-MS method for simultaneous determination of flavonoids and diterpenes in Egletes viscosa (L.) Less herbal products. J Pharm Biomed Anal. 2019 Mar 20;166:155-163. doi: 10.1016/j.jpba.2019.01.008. Epub 2019 Jan 8. PMID: 30654203. 15: Zakaria NNA, Okello EJ, Howes MJ, Birch-Machin MA, Bowman A. In vitro protective effects of an aqueous extract of Clitoria ternatea L. flower against hydrogen peroxide-induced cytotoxicity and UV-induced mtDNA damage in human keratinocytes. Phytother Res. 2018 Jun;32(6):1064-1072. doi: 10.1002/ptr.6045. Epub 2018 Feb 21. PMID: 29464849. 16: Sánchez-Murcia PA, Cortés-Cabrera Á, Gago F. Structural rationale for the cross-resistance of tumor cells bearing the A399V variant of elongation factor eEF1A1 to the structurally unrelated didemnin B, ternatin, nannocystin A and ansatrienin B. J Comput Aided Mol Des. 2017 Oct;31(10):915-928. doi: 10.1007/s10822-017-0066-x. Epub 2017 Sep 12. PMID: 28900796. 17: George S, Venkataraman R, Baby S. Melicodenine I, a new quinolinone alkaloid from Melicope denhamii leaves. Nat Prod Res. 2017 Apr;31(8):890-895. doi: 10.1080/14786419.2016.1253075. Epub 2016 Nov 6. PMID: 27817202. 18: Carelli JD, Sethofer SG, Smith GA, Miller HR, Simard JL, Merrick WC, Jain RK, Ross NT, Taunton J. Ternatin and improved synthetic variants kill cancer cells by targeting the elongation factor-1A ternary complex. Elife. 2015 Dec 10;4:e10222. doi: 10.7554/eLife.10222. PMID: 26651998; PMCID: PMC4786417. 19: Nair V, Bang WY, Schreckinger E, Andarwulan N, Cisneros-Zevallos L. Protective Role of Ternatin Anthocyanins and Quercetin Glycosides from Butterfly Pea (Clitoria ternatea Leguminosae) Blue Flower Petals against Lipopolysaccharide (LPS)-Induced Inflammation in Macrophage Cells. J Agric Food Chem. 2015 Jul 22;63(28):6355-65. doi: 10.1021/acs.jafc.5b00928. Epub 2015 Jul 10. PMID: 26120869. 20: Hiromoto T, Honjo E, Noda N, Tamada T, Kazuma K, Suzuki M, Blaber M, Kuroki R. Structural basis for acceptor-substrate recognition of UDP-glucose: anthocyanidin 3-O-glucosyltransferase from Clitoria ternatea. Protein Sci. 2015 Mar;24(3):395-407. doi: 10.1002/pro.2630. Epub 2015 Jan 28. PMID: 25556637; PMCID: PMC4353365.

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Boc-C1-PEG3-C4-OH