توفتسین

Tuftsin is a tetrapeptide (Thr-Lys-Pro-Arg, TKPR) located in the Fc-domain of the heavy chain of immunoglobulin G (residues 289-292). It has an immunostimulatory effect. It is named for Tufts University where it was first discovered in 1983.

Chemical data

Formula: C21H40N8O6
Molecular weight: 500.6 g/mol
IUPAC name: (2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid
SMILES: C[C@H]([C@@H](C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N)O
InChIKey: IESDGNYHXIOKRW-YXMSTPNBSA-N
XLogP: -7
Polar surface area: 252 Å²
H-bond donors: 8
H-bond acceptors: 9
Formal charge: 0

via PubChem

Research

689 papers

Helminth derivative tuftsin-phopshorylcholine to treat autoimmunity.Autoimmunity reviews · 2024
Tuftsin - Properties and Analogs.Current medicinal chemistry · 2017
FcγR-targeted tuftsin clusters rejuvenate macrophages in preclinical sepsis-associated secondary infection.Science translational medicine · 2025
[Tuftsin].Allergie und Immunologie · 1984
Tuftsin phosphorylcholine-a novel compound harnessing helminths to fight autoimmunity.Immunologic research · 2018

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 500.307

Show 3 more facts

chemical formula: C₂₁H₄₀N₈O₆
isomeric SMILES: C[C@H]([C@@H](C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N)O
canonical SMILES: CC(C(C(=O)NC(CCCCN)C(=O)N1CCCC1C(=O)NC(CCCN=C(N)N)C(=O)O)N)O

Sources (2)

via Wikidata · CC0