An anti-adipogenic cyclic peptide
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Ternatin

Item No. 20691

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo[N-methyl-L-alanyl-N-methyl-D-alanyl-(3R)-3-hydroxy-D-leucyl-D-alloisoleucyl-N-methyl-L-alanyl-N-methyl-L-leucyl-L-leucyl]
CAS Number
148619-41-4
Synonyms
  • 1,4,7,10,13,16,19-Heptaazacycloheneicosane
  • (‒)-Ternatin
Molecular Formula
C37H67N7O8
Formula Weight
738.0
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C(N[C@@H](CC(C)C)C(N(C)[C@H]1C)=O)[C@H](CC(C)C)N(C)C([C@H](C)N(C([C@]([C@H](CC)C)([H])NC([C@@](NC([C@@H](C)N(C)C1=O)=O)([H])[C@@H](C(C)C)O)=O)=O)C)=O
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
InChi Key
ZMFVAIFXJWEOMH-PTPSPKLBSA-N
Origin
Fungus/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $340

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    5 mg

    $1,191

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    Product Description

    Ternatin is a cyclic heptapeptide first isolated from the mushroom C. versicolor that has been shown to have cytotoxic and anti-adipogenic effects in vitro.1 It inhibits adipogenesis with an IC50 value of 27 nM and becomes cytotoxic to 3T3-L1 mouse adipocytes at 10-fold higher concentrations.1 Ternatin is reported to inhibit HCT116 cell proliferation with an IC50 value of 71 nM.2 Note that this metabolite should not be confused with the plant flavonoid of the same name.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shimokawa, K., Iwase, Y., Yamada, K., et al. Synthesis and inhibitory effect on fat accumulation of (−)-ternatin derivatives modified in the beta-OH-D-Leu7 moiety. Org. Biomol. Chem. 6(1), 58-60 (2008).

    2. Carelli, J.D., Sethofer, S.G., Smith, G.A., et al. Ternatin and improved synthetic variants kill cancer cells by targeting the elongation factor-1A ternary complex. eLife 4, e10222 (2015).