1.0 2011-09-21 01:52:00 UTC 2015-07-21 06:59:39 UTC FDB029216 Dynorphin B (10-13) Dynorphin B (10-13) is fraction of Dynorphin B with only Lys-Val-Val-Thr peptide chain. Dynorphin B is an agonist of nuclear opioid receptors coupling nuclear protein Kinase C activation to the transcription of cardiogenic genes in GTR1 embryonic stem cells Dynorphin B is a form of dynorphin.Dynorphins are a class of opioid peptides that arise from the precursor protein prodynorphin. When prodynorphin is cleaved during processing by proprotein convertase 2 (PC2), multiple active peptides are released: dynorphin A, dynorphin B, and a/b-neo-endorphin. Depolarization of a neuron containing prodynorphin stimulates PC2 processing, which occurs within synaptic vesicles in the presynaptic terminal. Occasionally, prodynorphin is not fully processed, leading to the release of "big dynorphin."This 32-amino acid molecule consists of both dynorphin A and dynorphin B.Dynorphin A, dynorphin B, and big dynorphin all contain a high proportion of basic amino acid residues, in particular lysine and arginine (29.4%, 23.1%, and 31.2% basic residues, respectively), as well as many hydrophobic residues (41.2%, 30.8%, and 34.4% hydrophobic residues, respectively). Although dynorphins are found widely distributed in the CNS, they have the highest concentrations in the hypothalamus, medulla, pons, midbrain, and spinal cord. Dynorphins are stored in large (80-120 nm diameter) dense-core vesicles that are considerably larger than vesicles storing neurotransmitters. These large dense-core vesicles differ from small synaptic vesicles in that a more intense and prolonged stimulus is needed to cause the large vesicles to release their contents into the synaptic cleft. Dense-core vesicle storage is characteristic of opioid peptides storage. The first clues to the functionality of dynorphins came from Goldstein et al. in their work with opioid peptides. The group discovered an endogenous opioid peptide in the porcine pituitary that proved difficult to isolate. By sequencing the first 13 amino acids of the peptide, they created a synthetic version of the peptide with a similar potency to the natural peptide. Goldstein et al. applied the synthetic peptide to the guinea ileum longitudinal muscle and found it to be an extraordinarily potent opioid peptide. The peptide was called dynorphin (from the Greek dynamis=power) to describe its potency. Dynorphins exert their effects primarily through the κ-opioid receptor (KOR), a G-protein-coupled receptor. Two subtypes of KORs have been identified: K1 and K2. Although KOR is the primary receptor for all dynorphins, the peptides do have some affinity for the μ-opioid receptor (MOR), d-opioid receptor (DOR), N-methyl-D-aspartic acid (NMDA)-type glutamate receptor . Different dynorphins show different receptor selectivities and potencies at receptors. Big dynorphin and dynorphin A have the same selectivity for human KOR, but dynorphin A is more selective for KOR over MOR and DOR than is big dynorphin. Big dynorphin is more potent at KORs than is dynorphin A. Both big dynorphin and dynorphin A are more potent and more selective than dynorphin B (from wiki) [HMDB] Lys-Val-Val-Thr C20H39N5O6 445.5536 445.290034005 (2S,3S)-2-[(2R)-2-[(2S)-2-[(2R)-2,6-diaminohexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid (2S,3S)-2-[(2R)-2-[(2S)-2-[(2R)-2,6-diaminohexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid CC(C)[C@H](NC(=O)[C@H](N)CCCCN)C(=O)N[C@H](C(C)C)C(=O)N[C@@H]([C@H](C)O)C(O)=O InChI=1S/C20H39N5O6/c1-10(2)14(23-17(27)13(22)8-6-7-9-21)18(28)24-15(11(3)4)19(29)25-16(12(5)26)20(30)31/h10-16,26H,6-9,21-22H2,1-5H3,(H,23,27)(H,24,28)(H,25,29)(H,30,31)/t12-,13+,14-,15+,16-/m0/s1 VSLCIGXQLCYQTD-NPJQDHAYSA-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 acyclic compounds Alpha amino acid amides Amino acids Beta hydroxy acids and derivatives Branched fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Monoalkylamines Monocarboxylic acids and derivatives N-acyl amines N-acyl-L-alpha-amino acids Organic oxides Organopnictogen compounds Secondary alcohols Secondary carboxylic acid amides Short-chain hydroxy acids and derivatives Valine and derivatives Alcohol Aliphatic acyclic compound Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Beta-hydroxy acid Branched fatty acid Carbonyl group Carboxamide group Carboxylic acid Fatty acid Fatty acyl Fatty amide Hydrocarbon derivative Hydroxy acid 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-substituted-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary alcohol Secondary carboxylic acid amide Short-chain hydroxy acid Valine or derivatives Solid logp -1.55 ALOGPS logs -2.94 ALOGPS solubility 5.13e-01 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 3.3 ChemAxon pka_strongest_basic 10.2 ChemAxon iupac (2S,3S)-2-[(2R)-2-[(2S)-2-[(2R)-2,6-diaminohexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid ChemAxon average_mass 445.5536 ChemAxon mono_mass 445.290034005 ChemAxon smiles CC(C)[C@H](NC(=O)[C@H](N)CCCCN)C(=O)N[C@H](C(C)C)C(=O)N[C@@H]([C@H](C)O)C(O)=O ChemAxon formula C20H39N5O6 ChemAxon inchi InChI=1S/C20H39N5O6/c1-10(2)14(23-17(27)13(22)8-6-7-9-21)18(28)24-15(11(3)4)19(29)25-16(12(5)26)20(30)31/h10-16,26H,6-9,21-22H2,1-5H3,(H,23,27)(H,24,28)(H,25,29)(H,30,31)/t12-,13+,14-,15+,16-/m0/s1 ChemAxon inchikey VSLCIGXQLCYQTD-NPJQDHAYSA-N ChemAxon polar_surface_area 196.87 ChemAxon refractivity 113.66 ChemAxon polarizability 47.56 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 8 ChemAxon donor_count 7 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 98178 Specdb::NmrOneD 98179 Specdb::NmrOneD 98180 Specdb::NmrOneD 98181 Specdb::NmrOneD 98182 Specdb::NmrOneD 98183 Specdb::NmrOneD 98184 Specdb::NmrOneD 98185 Specdb::NmrOneD 98186 Specdb::NmrOneD 98187 Specdb::NmrOneD 98188 Specdb::NmrOneD 98189 Specdb::NmrOneD 98190 Specdb::NmrOneD 98191 Specdb::NmrOneD 98192 Specdb::NmrOneD 98193 Specdb::NmrOneD 98194 Specdb::NmrOneD 98195 Specdb::NmrOneD 98196 Specdb::NmrOneD 98197 Specdb::MsMs 312433 Specdb::MsMs 312434 Specdb::MsMs 312435 Specdb::MsMs 357691 Specdb::MsMs 357692 Specdb::MsMs 357693 Specdb::MsMs 2432086 Specdb::MsMs 2432087 Specdb::MsMs 2432088 Specdb::MsMs 2503547 Specdb::MsMs 2503548 Specdb::MsMs 2503549 Specdb::CMs 20848 Specdb::CMs 40019 Specdb::CMs 174136 HMDB12936