1.0 2011-09-21 01:52:00 UTC 2015-07-21 06:59:39 UTC FDB029217 Dynorphin B (6-9) Dynorphin B (6-9) is fraction of Dynorphin B with only Arg-Arg-Gln-Phe 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] Arg-Arg-Gln-Phe C26H43N11O6 605.6897 605.339778163 (2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-(C-hydroxycarbonimidoyl)butanamido]-3-phenylpropanoic acid (2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-(C-hydroxycarbonimidoyl)butanamido]-3-phenylpropanoic acid N[C@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](CCC(O)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O InChI=1S/C26H43N11O6/c27-16(8-4-12-33-25(29)30)21(39)35-17(9-5-13-34-26(31)32)22(40)36-18(10-11-20(28)38)23(41)37-19(24(42)43)14-15-6-2-1-3-7-15/h1-3,6-7,16-19H,4-5,8-14,27H2,(H2,28,38)(H,35,39)(H,36,40)(H,37,41)(H,42,43)(H4,29,30,33)(H4,31,32,34)/t16-,17+,18-,19+/m1/s1 YTMBNLHIDIKJIU-HCXYKTFWSA-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 Alpha amino acid amides Amino acids Amphetamines and derivatives Carbonyl compounds Carboximidamides Carboxylic acids Glutamine and derivatives Guanidines Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives N-acyl amines N-acyl-L-alpha-amino acids Organic oxides Organopnictogen compounds Phenylalanine and derivatives Phenylpropanoic acids Primary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Secondary carboxylic acid amides 3-phenylpropanoic-acid Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Amphetamine or derivatives Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboximidamide Carboxylic acid Fatty acyl Fatty amide Glutamine or derivatives Guanidine Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety 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 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalanine or derivatives Primary aliphatic amine Primary amine Primary carboxylic acid amide Propargyl-type 1,3-dipolar organic compound Secondary carboxylic acid amide Solid logp -3.30 ALOGPS logs -3.61 ALOGPS solubility 1.47e-01 g/l ALOGPS logp -7 ChemAxon pka_strongest_acidic -0.27 ChemAxon pka_strongest_basic 12.73 ChemAxon iupac (2S)-2-[(2R)-2-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-4-(C-hydroxycarbonimidoyl)butanamido]-3-phenylpropanoic acid ChemAxon average_mass 605.6897 ChemAxon mono_mass 605.339778163 ChemAxon smiles N[C@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](CCC(O)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O ChemAxon formula C26H43N11O6 ChemAxon inchi InChI=1S/C26H43N11O6/c27-16(8-4-12-33-25(29)30)21(39)35-17(9-5-13-34-26(31)32)22(40)36-18(10-11-20(28)38)23(41)37-19(24(42)43)14-15-6-2-1-3-7-15/h1-3,6-7,16-19H,4-5,8-14,27H2,(H2,28,38)(H,35,39)(H,36,40)(H,37,41)(H,42,43)(H4,29,30,33)(H4,31,32,34)/t16-,17+,18-,19+/m1/s1 ChemAxon inchikey YTMBNLHIDIKJIU-HCXYKTFWSA-N ChemAxon polar_surface_area 318.5 ChemAxon refractivity 187.41 ChemAxon polarizability 62.93 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 14 ChemAxon donor_count 13 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 98198 Specdb::NmrOneD 98199 Specdb::NmrOneD 98200 Specdb::NmrOneD 98201 Specdb::NmrOneD 98202 Specdb::NmrOneD 98203 Specdb::NmrOneD 98204 Specdb::NmrOneD 98205 Specdb::NmrOneD 98206 Specdb::NmrOneD 98207 Specdb::NmrOneD 98208 Specdb::NmrOneD 98209 Specdb::NmrOneD 98210 Specdb::NmrOneD 98211 Specdb::NmrOneD 98212 Specdb::NmrOneD 98213 Specdb::NmrOneD 98214 Specdb::NmrOneD 98215 Specdb::NmrOneD 98216 Specdb::NmrOneD 98217 Specdb::MsMs 320080 Specdb::MsMs 320081 Specdb::MsMs 320082 Specdb::MsMs 367393 Specdb::MsMs 367394 Specdb::MsMs 367395 Specdb::MsMs 2710328 Specdb::MsMs 2710329 Specdb::MsMs 2710330 Specdb::MsMs 2994998 Specdb::MsMs 2994999 Specdb::MsMs 2995000 Specdb::CMs 24441 Specdb::CMs 40020 Specdb::CMs 476878 Specdb::CMs 476879 Specdb::CMs 476880 Specdb::CMs 476881 Specdb::CMs 476882 Specdb::CMs 476883 Specdb::CMs 476884 Specdb::CMs 476885 Specdb::CMs 476886 Specdb::CMs 476887 Specdb::CMs 476888 Specdb::CMs 476889 Specdb::CMs 476890 Specdb::CMs 476891 Specdb::CMs 476892 Specdb::CMs 476893 Specdb::CMs 476894 Specdb::CMs 476895 Specdb::CMs 476896 Specdb::CMs 476897 Specdb::CMs 476898 Specdb::CMs 476899 Specdb::CMs 476900 HMDB12937