1.0 2011-09-21 01:52:01 UTC 2015-07-21 06:59:39 UTC FDB029218 Dynorphin B 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] prodynorphin 228-240 rimorphin Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Gln-Phe-Lys-Val-Val-Thr C74H115N21O17 1570.8354 1569.877981359 (2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2R)-2-{2-[(2R)-2-[(2R)-2-(2-{2-[(2R)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-[(diaminomethylidene)amino]pentanamido}-5-[(diaminomethylidene)amino]pentanamido]-4-carbamoylbutanamido]-3-phenylpropanamido}hexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid (2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2R)-2-{2-[(2R)-2-[(2R)-2-(2-{2-[(2R)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-[(diaminomethylidene)amino]pentanamido}-5-[(diaminomethylidene)amino]pentanamido]-4-carbamoylbutanamido]-3-phenylpropanamido}hexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid 85006-82-2 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)NC(CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)NC(CC1=CC=CC=C1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O InChI=1S/C74H115N21O17/c1-40(2)34-53(91-68(107)54(36-44-18-10-8-11-19-44)86-58(100)39-84-57(99)38-85-62(101)48(76)35-46-25-27-47(97)28-26-46)67(106)89-51(24-17-33-83-74(80)81)63(102)87-50(23-16-32-82-73(78)79)64(103)90-52(29-30-56(77)98)65(104)92-55(37-45-20-12-9-13-21-45)69(108)88-49(22-14-15-31-75)66(105)93-59(41(3)4)70(109)94-60(42(5)6)71(110)95-61(43(7)96)72(111)112/h8-13,18-21,25-28,40-43,48-55,59-61,96-97H,14-17,22-24,29-39,75-76H2,1-7H3,(H2,77,98)(H,84,99)(H,85,101)(H,86,100)(H,87,102)(H,88,108)(H,89,106)(H,90,103)(H,91,107)(H,92,104)(H,93,105)(H,94,109)(H,95,110)(H,111,112)(H4,78,79,82)(H4,80,81,83)/t43-,48-,49+,50-,51?,52+,53-,54-,55?,59+,60+,61+/m1/s1 AGTSSZRZBSNTGQ-QHDWWRMQSA-N belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Polypeptides Organic compounds Organic Polymers Polypeptides Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alpha amino acid amides Amino acids Amphetamines and derivatives Aralkylamines Beta hydroxy acids and derivatives Carbonyl compounds Carboximidamides Carboxylic acids Glutamine and derivatives Guanidines Hydrocarbon derivatives Leucine and derivatives Monoalkylamines Monocarboxylic acids and derivatives N-acyl amines N-acyl-L-alpha-amino acids Organic oxides Organopnictogen compounds Peptides Phenylalanine and derivatives Primary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Secondary alcohols Secondary carboxylic acid amides Tyrosine and derivatives Valine and derivatives 1-hydroxy-2-unsubstituted benzenoid Alcohol Alpha peptide Alpha-amino acid amide Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Benzenoid Beta-hydroxy acid Carbonyl group Carboxamide group Carboximidamide Carboxylic acid Carboxylic acid derivative Fatty acyl Fatty amide Glutamine or derivatives Guanidine Hydrocarbon derivative Hydroxy acid Leucine or derivatives 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 Phenol Phenylalanine or derivatives Polypeptide Primary aliphatic amine Primary amine Primary carboxylic acid amide Propargyl-type 1,3-dipolar organic compound Secondary alcohol Secondary carboxylic acid amide Tyrosine or derivatives Valine or derivatives Solid logp -1.29 ALOGPS logs -5.08 ALOGPS solubility 1.31e-02 g/l ALOGPS logp -7.6 ChemAxon pka_strongest_acidic 3.29 ChemAxon pka_strongest_basic 11.16 ChemAxon iupac (2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2R)-2-{2-[(2R)-2-[(2R)-2-(2-{2-[(2R)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanamido]-5-[(diaminomethylidene)amino]pentanamido}-5-[(diaminomethylidene)amino]pentanamido]-4-carbamoylbutanamido]-3-phenylpropanamido}hexanamido]-3-methylbutanamido]-3-methylbutanamido]-3-hydroxybutanoic acid ChemAxon average_mass 1570.8354 ChemAxon mono_mass 1569.877981359 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)NC(CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)NC(CC1=CC=CC=C1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O ChemAxon formula C74H115N21O17 ChemAxon inchi InChI=1S/C74H115N21O17/c1-40(2)34-53(91-68(107)54(36-44-18-10-8-11-19-44)86-58(100)39-84-57(99)38-85-62(101)48(76)35-46-25-27-47(97)28-26-46)67(106)89-51(24-17-33-83-74(80)81)63(102)87-50(23-16-32-82-73(78)79)64(103)90-52(29-30-56(77)98)65(104)92-55(37-45-20-12-9-13-21-45)69(108)88-49(22-14-15-31-75)66(105)93-59(41(3)4)70(109)94-60(42(5)6)71(110)95-61(43(7)96)72(111)112/h8-13,18-21,25-28,40-43,48-55,59-61,96-97H,14-17,22-24,29-39,75-76H2,1-7H3,(H2,77,98)(H,84,99)(H,85,101)(H,86,100)(H,87,102)(H,88,108)(H,89,106)(H,90,103)(H,91,107)(H,92,104)(H,93,105)(H,94,109)(H,95,110)(H,111,112)(H4,78,79,82)(H4,80,81,83)/t43-,48-,49+,50-,51?,52+,53-,54-,55?,59+,60+,61+/m1/s1 ChemAxon inchikey AGTSSZRZBSNTGQ-QHDWWRMQSA-N ChemAxon polar_surface_area 650.89 ChemAxon refractivity 408.73 ChemAxon polarizability 167.61 ChemAxon rotatable_bond_count 51 ChemAxon acceptor_count 25 ChemAxon donor_count 22 ChemAxon physiological_charge 3 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 321487 Specdb::MsMs 321488 Specdb::MsMs 321489 Specdb::MsMs 369130 Specdb::MsMs 369131 Specdb::MsMs 369132 Specdb::MsMs 2803159 Specdb::MsMs 2803160 Specdb::MsMs 2803161 Specdb::MsMs 2879594 Specdb::MsMs 2879595 Specdb::MsMs 2879596 Specdb::NmrOneD 98218 Specdb::NmrOneD 98219 Specdb::NmrOneD 98220 Specdb::NmrOneD 98221 Specdb::NmrOneD 98222 Specdb::NmrOneD 98223 Specdb::NmrOneD 98224 Specdb::NmrOneD 98225 Specdb::NmrOneD 98226 Specdb::NmrOneD 98227 Specdb::NmrOneD 98228 Specdb::NmrOneD 98229 Specdb::NmrOneD 98230 Specdb::NmrOneD 98231 Specdb::NmrOneD 98232 Specdb::NmrOneD 98233 Specdb::NmrOneD 98234 Specdb::NmrOneD 98235 Specdb::NmrOneD 98236 Specdb::NmrOneD 98237 HMDB12938