1.0 2011-09-21 00:13:16 UTC 2015-07-21 06:57:11 UTC FDB022389 Enkephalin L Enkephalin L is an opioid peptide. Opioid peptides are a group of neuropeptides which include enkephalins, endorphins and dynorphins. In addition to their central and peripheral antinociceptive function, opioids can modulate immune activity and cell proliferation. Enkephalins typically have a turnover rate measured in seconds to minutes, both in vivo and in vitro, and this stability is related to the age of the cell system under study. It is noteworthy that the residues most essential to enkephalin function are also either neurotransmitters themselves (glycine) or immediate precursors of L-Dopa, dopamine and norepinephrine (tyrosine and phenylalanine). The variable fifth amino acid leucine (leu5) or methionine (met5) has not yet been assigned any neurotransmitter candidacy. Again, this suggests that enkephalin is polyfunctional in that, in its intact state it elicits binding to the same sites in the brain as morphine and other opiates, and its degradation products have a potential for follow-up accessory functions by reacting as signaling entities themselves, or as the immediate precursors to inhibitory or metabotropic neurotransmitters. Enkephalins are present in macrophages infiltrating the dermal papillae in involved psoriatic skin and that the amount of enkephalin is significantly increased in involved psoriatic skin. Major enkephalin pathways in the brain involve the extrapyramidal system, including motor pathways controlled by the basal ganglia, the limbic system that governs emotional and behavioral control, and the hypothalamic-neuroendocrine axis. The apparent overlap of localization within the central nervous system of dopaminergic, glycinergic, and enkephalinergic pathways is speculated to be of neurophysiological significance, especially in light of the relatively short half-life of the enkephalins and the immediate precursor-product relationship between tyrosine and dopamine, and glycinergic signaling. Enkephalins are released into the bloodstream of mammals by the adrenal medulla. Once they are in the blood, these peptides undergo a fairly rapid hydrolysis by several plasma-contained enzymes. However, a fraction of the enkephalins present in the plasma are bound to the serum albumin, and the bound peptides are almost completely intact even after a long incubation in the presence of serum enzymes. (PMID: 9450624, 16802191, 4069309) [HMDB] [5-Leucine]Enkephalin [Leu 5]enkephalin [leu]enkephalin [Leu5]-Enkephalin Leucine enkephalin C28H37N5O7 555.6227 555.269298563 (2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid (2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid 14-18-6 CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1 URLZCHNOLZSCCA-VABKMULXSA-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 Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alpha amino acid amides Amino acids Amphetamines and derivatives Aralkylamines Carbonyl compounds Carboxylic acids Fatty amides Hydrocarbon derivatives Leucine and derivatives Monoalkylamines Monocarboxylic acids and derivatives N-acyl-L-alpha-amino acids Organic oxides Organopnictogen compounds Phenylalanine and derivatives Secondary carboxylic acid amides Tyrosine and derivatives 1-hydroxy-2-unsubstituted benzenoid Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid Fatty acyl Fatty amide Hydrocarbon derivative Leucine or derivatives Monocarboxylic acid or derivatives Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-l-alpha-amino acid N-substituted-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Phenylalanine or derivatives Primary aliphatic amine Primary amine Secondary carboxylic acid amide Tyrosine or derivatives Solid logp -1.05 ALOGPS logs -4.58 ALOGPS solubility 1.46e-02 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 3.7 ChemAxon pka_strongest_basic 7.73 ChemAxon iupac (2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid ChemAxon average_mass 555.6227 ChemAxon mono_mass 555.269298563 ChemAxon smiles CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O ChemAxon formula C28H37N5O7 ChemAxon inchi InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1 ChemAxon inchikey URLZCHNOLZSCCA-VABKMULXSA-N ChemAxon polar_surface_area 199.95 ChemAxon refractivity 145.59 ChemAxon polarizability 57.94 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 8 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 307489 Specdb::MsMs 307490 Specdb::MsMs 307491 Specdb::MsMs 351454 Specdb::MsMs 351455 Specdb::MsMs 351456 Specdb::MsMs 2690159 Specdb::MsMs 2690160 Specdb::MsMs 2690161 Specdb::MsMs 2988119 Specdb::MsMs 2988120 Specdb::MsMs 2988121 Specdb::NmrOneD 146190 Specdb::NmrOneD 146191 Specdb::NmrOneD 146192 Specdb::NmrOneD 146193 Specdb::NmrOneD 146194 Specdb::NmrOneD 146195 Specdb::NmrOneD 146196 Specdb::NmrOneD 146197 Specdb::NmrOneD 146198 Specdb::NmrOneD 146199 Specdb::NmrOneD 146200 Specdb::NmrOneD 146201 Specdb::NmrOneD 146202 Specdb::NmrOneD 146203 Specdb::NmrOneD 146204 Specdb::NmrOneD 146205 Specdb::NmrOneD 146206 Specdb::NmrOneD 146207 Specdb::NmrOneD 146208 Specdb::NmrOneD 146209 Specdb::CMs 18686 Specdb::CMs 37902 Specdb::CMs 281930 Specdb::CMs 339941 Specdb::CMs 339942 Specdb::CMs 339943 Specdb::CMs 339944 Specdb::CMs 339945 Specdb::CMs 339946 Specdb::CMs 339947 Specdb::CMs 339948 Specdb::CMs 339949 Specdb::CMs 339950 Specdb::CMs 339951 Specdb::CMs 339952 Specdb::CMs 339953 Specdb::CMs 339954 Specdb::CMs 339955 Specdb::CMs 339956 Specdb::CMs 339957 Specdb::CMs 339958 Specdb::CMs 339959 Specdb::CMs 339960 Specdb::CMs 339961 Specdb::CMs 339962 HMDB01045 #<Reference:0x000055ce30d38840> #<Reference:0x000055ce30d38688> #<Reference:0x000055ce30d384d0> 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