1.0 2011-09-21 00:26:11 UTC 2015-07-21 06:57:35 UTC FDB023200 VPGPR Enterostatin Enterostatin VPGPR (Val-Pro-Gly-Pro-Arg) is a pentapeptide released from procolipase during fat digestion. In addition to the pancreas, enterostatin-immunoreactive cells are also present in the antrum and proximal small intestine. Enterostatin selectively reduces fat intake, decreases insulin secretion, and also increases energy expenditure by activating brown adipose tissue during high-fat feeding. Enterostatins are pentapeptides derived from the NH2-terminus of procolipase after tryptic cleavage and belong to the family of gut-brain peptides. Enterostatin is generated by the action of trypsin on procolipase in the intestinal lumen. Its structure is highly conserved in evolution, with an amino acid sequence of XPXPR. Three enterostatin sequences, Val-Pro-Asp-Pro-Arg (VPDPR), Val-Pro-Gly-Pro-Arg (VPGPR), and Ala-Pro-Gly-Pro-Arg (APGPR), have been studied extensively and shown to be almost equally effective in their ability to decrease dietary fat preference. Enterostatins are selective inhibitors of appetite, particularly of fat intake. Hyperenterostatinemia in obesity is probably secondary to enterostatin resistance; therefore, the regulatory system is producing more enterostatin to counteract the resistance. This is very similar to hyperinsulinemia and hyperleptinemia in obesity. The diminution in the meal-induced secretion of enterostatin in obesity suggests a delay in the appearance of satiety, leading to increased caloric intake. In rats enterostatin decreases body weight by decreasing fat-calorie intake and increasing the sympathetic firing rate of the nerves in interscapular brown adipose tissue. Enterostatin levels are elevated in the plasma of obese women, and enterostatin secretion is diminished after satiety. Oral administration of enterostatin, however, has no effect on food intake, energy expenditure, or body weight in subjects with a preference for a high-fat diet experiencing a negative energy and fat balance, and the physiology of enterostatin in humans remains to be defined. (PMID: 10084574, 9526102, 8886249) [HMDB] 2-[1-[N-(1-L-valyl-L-prolyl)glycyl]-L-prolyl]-L-Arginine L-valyl-L-prolylglycyl-L-prolyl-L-Arginine C23H40N8O6 524.6137 524.307081052 (2S)-2-{[(2S)-1-(2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid (2S)-2-{[(2S)-1-(2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid 144964-56-7 CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(O)=O InChI=1S/C23H40N8O6/c1-13(2)18(24)21(35)31-11-5-7-15(31)19(33)28-12-17(32)30-10-4-8-16(30)20(34)29-14(22(36)37)6-3-9-27-23(25)26/h13-16,18H,3-12,24H2,1-2H3,(H,28,33)(H,29,34)(H,36,37)(H4,25,26,27)/t14-,15-,16-,18-/m0/s1 QVZKZDOWTVQTPL-OVWQWFNUSA-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 Branched fatty acids Carbonyl compounds Carboximidamides Carboxylic acids Guanidines Heterocyclic fatty acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives N-acyl-L-alpha-amino acids N-acylpyrrolidines Organic oxides Organopnictogen compounds Proline and derivatives Propargyl-type 1,3-dipolar organic compounds Pyrrolidinecarboxamides Secondary carboxylic acid amides Tertiary carboxylic acid amides Valine and derivatives Aliphatic heteromonocyclic compound Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Azacycle Branched fatty acid Carbonyl group Carboxamide group Carboximidamide Carboxylic acid Fatty acid Fatty acyl Guanidine Heterocyclic fatty acid Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid 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 carboxylic acid amide Tertiary carboxylic acid amide Valine or derivatives Solid logp -2.71 ALOGPS logs -3.13 ALOGPS solubility 3.88e-01 g/l ALOGPS logp -4.5 ChemAxon pka_strongest_acidic 3.49 ChemAxon pka_strongest_basic 11.25 ChemAxon iupac (2S)-2-{[(2S)-1-(2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid ChemAxon average_mass 524.6137 ChemAxon mono_mass 524.307081052 ChemAxon smiles CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(O)=O ChemAxon formula C23H40N8O6 ChemAxon inchi InChI=1S/C23H40N8O6/c1-13(2)18(24)21(35)31-11-5-7-15(31)19(33)28-12-17(32)30-10-4-8-16(30)20(34)29-14(22(36)37)6-3-9-27-23(25)26/h13-16,18H,3-12,24H2,1-2H3,(H,28,33)(H,29,34)(H,36,37)(H4,25,26,27)/t14-,15-,16-,18-/m0/s1 ChemAxon inchikey QVZKZDOWTVQTPL-OVWQWFNUSA-N ChemAxon polar_surface_area 226.54 ChemAxon refractivity 132.7 ChemAxon polarizability 54.6 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9375 Specdb::CMs 38634 Specdb::NmrOneD 28342 Specdb::NmrOneD 28343 Specdb::NmrOneD 28344 Specdb::NmrOneD 28345 Specdb::NmrOneD 28346 Specdb::NmrOneD 28347 Specdb::NmrOneD 28348 Specdb::NmrOneD 28349 Specdb::NmrOneD 28350 Specdb::NmrOneD 28351 Specdb::NmrOneD 28352 Specdb::NmrOneD 28353 Specdb::NmrOneD 28354 Specdb::NmrOneD 28355 Specdb::NmrOneD 28356 Specdb::NmrOneD 28357 Specdb::NmrOneD 28358 Specdb::NmrOneD 28359 Specdb::NmrOneD 28360 Specdb::NmrOneD 28361 Specdb::MsMs 286690 Specdb::MsMs 286691 Specdb::MsMs 286692 Specdb::MsMs 325342 Specdb::MsMs 325343 Specdb::MsMs 325344 Specdb::MsMs 2726825 Specdb::MsMs 2726826 Specdb::MsMs 2726827 Specdb::MsMs 2979395 Specdb::MsMs 2979396 Specdb::MsMs 2979397 HMDB03577 #<Reference:0x000055ce316720a0> #<Reference:0x000055ce31671ee8> #<Reference:0x000055ce31671d30> 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