(-)-Ternatin

Base Information

• Chemical Name: (-)-Ternatin
• CAS No.: 148619-41-4
• Molecular Formula: C₃₇H₆₇N₇O₈
• Molecular Weight: 737.981
• ChEMBL ID: CHEMBL394301
• DSSTox Substance ID: DTXSID20933442
• Metabolomics Workbench ID: 118666
• Nikkaji Number: J2.234.308D
• Wikidata: Q75057788
• Mol file: 148619-41-4.mol

Synonyms:cyclo(-OH-Leu-Ile-(NMe)Ala-(NMe)Leu-Leu-(NMe)Ala-(NMe)Ala-);cyclo(-OH-leucyl-isoleucyl-(N-methyl)alanyl-(N-methyl)leucyl-leucyl-(N-methyl)alanyl-(N-methyl)alanyl-);ternatin heptapeptide

Chemical Property of (-)-Ternatin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 985.4°C at 760 mmHg
• PKA: 12.83±0.70(Predicted)
• Flash Point: 549.7°C
• PSA: 26.02000
• Density: 1.028g/cm³
• LogP: 3.07860
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 737.50511212
• Heavy Atom Count: 52
• Complexity: 1290

Purity/Quality:

98%Min ^*data from raw suppliers

Ternatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C1C(=O)N(C(C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)NC(C(=O)N1)C(C(C)C)O)C)C)C)C)CC(C)C)CC(C)C)C)C)C
• Isomeric SMILES: CC[C@H](C)[C@@H]1C(=O)N([C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N([C@@H](C(=O)N[C@@H](C(=O)N1)[C@@H](C(C)C)O)C)C)C)C)CC(C)C)CC(C)C)C)C)C
• General Description: Ternatin heptapeptide, also known as (-)-Ternatin, is a highly N-methylated cyclic heptapeptide derived from *Coriolus versicolor* that acts as a potent inhibitor of fat accumulation in adipocytes. It localizes to specific organelles in 3T3-L1 murine preadipocytes, where it likely exerts its anti-adipogenic effects, demonstrating moderate inhibitory activity (IC50 = 23 μM) without significant cytotoxicity. Its FITC-labeled analog retains bioactivity, while structural modifications, such as replacing the peptide core with a methyl ester group, abolish its function.

Technology Process of (-)-Ternatin

There total 11 articles about (-)-Ternatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C37H69N7O9 (949897-55-6) → (-)-ternatin (148619-41-4)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane;

DOI:10.1016/j.bmcl.2007.06.015

Reference yield: 81.0%

(3S,6S,9S,12S,15R,18R,21R)-18-((R)-1-Benzyloxy-2-methyl-propyl)-15-((S)-sec-butyl)-6,9-diisobutyl-1,3,4,10,12,13,21-heptamethyl-1,4,7,10,13,16,19-heptaaza-cyclohenicosane-2,5,8,11,14,17,20-heptaone → (-)-ternatin (148619-41-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

DOI:10.1016/j.tetlet.2006.04.073

Reference yield:

(2R,3R)-(+)-ethyl 2-azido-3-isopropyl-3-hydroxypropionate (159990-09-7) → (-)-ternatin (148619-41-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / H₂ / Pd/C / methanol

2: 83 percent / PyBroP; DIPEA / CH₂Cl₂

3: TFA / CH₂Cl₂

4: HATU; DIPEA / CH₂Cl₂

5: 84 percent / aq. NaOH / methanol

6: 88 percent / HATU; DIPEA / CH₂Cl₂

7: 100 percent / aq. LiOH / 2-methyl-propan-2-ol; tetrahydrofuran

8: 100 percent / TFA / CH₂Cl₂

9: 100 percent / HATU; HOAt; DIPEA / CH₂Cl₂

With lithium hydroxide; sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2007.06.015

upstream raw materials:

C₃₇H₆₉N₇O₉

C₁₉H₃₅N₃O₇

C₄₃H₇₉N₇O₁₁

C₁₇H₃₂N₂O₆

Refernces

Application of FITC-labeled ternatin on its cellular localization in 3T3-L1 murine preadipocytes

10.1246/cl.2009.150

This study investigated the cellular localization of (?)-ternatin, a potent inhibitor of fat accumulation, in 3T3-L1 murine preadipocytes. (?)-ternatin is a highly N-methylated cyclic heptapeptide isolated from the mushroom Coriolus versicolor, which has been shown to inhibit fat accumulation in vitro and in vivo. To explore its cellular localization, FITC-labeled ternatin (3) was synthesized from a highly bioactive ternatin analog (2) and a FITC-linker conjugate (5) using click chemistry. FITC-labeled ternatin was found to localize in specific organelles of 3T3-L1 cells, suggesting that (?)-ternatin exerts its biological activity there. A negative control compound (7) was also synthesized in which the peptide core was substituted with a methyl ester group. The results showed that FITC-labeled ternatin (3) had a moderate inhibitory effect on fat accumulation with an IC50 value of 23 mM and no significant cytotoxicity, while the negative control (7) had no inhibitory effect or cytotoxicity.