1.0 2011-09-21 00:34:18 UTC 2015-07-21 06:57:50 UTC FDB023760 Tuftsin Tuftsin (L-threonyl-L-lysyl-L-prolyl-L-arginine) is a peptide related primarily to the immune system function. Tuftsin is a tetrapeptide (Thr-Lys-Pro-Arg) produced by enzymatic cleavage of the Fc-domain of the heavy chain of immunoglobulin G. It is produced primarily in the spleen. Its biological activity is related primarily to the immune system function. Tuftsin binds to specific receptors on the surface of macrophages and polymorphonuclear leukocytes, stimulating their migration, phagocytic, bactericidal, and tumoricidal activity. It also influences antibody formation. Tuftsin deficiency, either hereditary or following splenectomy, results in increased susceptibility to certain infections. Tuftsin has been chemically synthesized and it is considered for use in immunotherapy. [HMDB] L-threonyl-l-LYSYL-l-prolyl-l-arginine Polytuftsin Tuftsin polymer C21H40N8O6 500.5923 500.307081052 (2S)-2-{[(2S)-1-{6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanoyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid (2S)-2-{[(2S)-1-{6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanoyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid 112592-90-2 C[C@@H](O)[C@H](N)C(=O)NC(CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(O)=O InChI=1S/C21H40N8O6/c1-12(30)16(23)18(32)27-13(6-2-3-9-22)19(33)29-11-5-8-15(29)17(31)28-14(20(34)35)7-4-10-26-21(24)25/h12-16,30H,2-11,22-23H2,1H3,(H,27,32)(H,28,31)(H,34,35)(H4,24,25,26)/t12-,13?,14+,15+,16+/m1/s1 IESDGNYHXIOKRW-NNFXCFJSSA-N belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Oligopeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic heteromonocyclic compounds Alpha amino acid amides Amino acids Azacyclic compounds Carbonyl compounds Carboximidamides Carboxylic acids Guanidines Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids Monoalkylamines Monocarboxylic acids and derivatives N-acyl amines N-acyl-L-alpha-amino acids N-acylpyrrolidines Organic oxides Organopnictogen compounds Proline and derivatives Propargyl-type 1,3-dipolar organic compounds Pyrrolidinecarboxamides Secondary alcohols Secondary carboxylic acid amides Tertiary carboxylic acid amides Alcohol Aliphatic heteromonocyclic compound Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Azacycle Carbonyl group Carboxamide group Carboximidamide Carboxylic acid Fatty acid Fatty acyl Fatty amide Guanidine Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-acyl-l-alpha-amino acid N-acylpyrrolidine Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Proline or derivatives Propargyl-type 1,3-dipolar organic compound Pyrrolidine Pyrrolidine carboxylic acid or derivatives Pyrrolidine-2-carboxamide Secondary alcohol Secondary carboxylic acid amide Tertiary carboxylic acid amide Solid logp -3.31 ALOGPS logs -3.31 ALOGPS solubility 2.46e-01 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 3.44 ChemAxon pka_strongest_basic 11.9 ChemAxon iupac (2S)-2-{[(2S)-1-{6-amino-2-[(2S,3R)-2-amino-3-hydroxybutanamido]hexanoyl}pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid ChemAxon average_mass 500.5923 ChemAxon mono_mass 500.307081052 ChemAxon smiles C[C@@H](O)[C@H](N)C(=O)NC(CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(O)=O ChemAxon formula C21H40N8O6 ChemAxon inchi InChI=1S/C21H40N8O6/c1-12(30)16(23)18(32)27-13(6-2-3-9-22)19(33)29-11-5-8-15(29)17(31)28-14(20(34)35)7-4-10-26-21(24)25/h12-16,30H,2-11,22-23H2,1H3,(H,27,32)(H,28,31)(H,34,35)(H4,24,25,26)/t12-,13?,14+,15+,16+/m1/s1 ChemAxon inchikey IESDGNYHXIOKRW-NNFXCFJSSA-N ChemAxon polar_surface_area 249.98 ChemAxon refractivity 136.78 ChemAxon polarizability 52.58 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 11 ChemAxon donor_count 9 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26061 Specdb::CMs 38874 Specdb::NmrOneD 55022 Specdb::NmrOneD 55023 Specdb::NmrOneD 55024 Specdb::NmrOneD 55025 Specdb::NmrOneD 55026 Specdb::NmrOneD 55027 Specdb::NmrOneD 55028 Specdb::NmrOneD 55029 Specdb::NmrOneD 55030 Specdb::NmrOneD 55031 Specdb::NmrOneD 55032 Specdb::NmrOneD 55033 Specdb::NmrOneD 55034 Specdb::NmrOneD 55035 Specdb::NmrOneD 55036 Specdb::NmrOneD 55037 Specdb::NmrOneD 55038 Specdb::NmrOneD 55039 Specdb::NmrOneD 55040 Specdb::NmrOneD 55041 Specdb::MsMs 323731 Specdb::MsMs 323732 Specdb::MsMs 323733 Specdb::MsMs 371965 Specdb::MsMs 371966 Specdb::MsMs 371967 Specdb::MsMs 2778736 Specdb::MsMs 2778737 Specdb::MsMs 2778738 Specdb::MsMs 2904024 Specdb::MsMs 2904025 Specdb::MsMs 2904026 HMDB05770 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823