Human Metabolome Database Version 3.5

Showing metabocard for Dynorphin B (HMDB12938)

Record Information
Version 3.5
Creation Date 2009-07-24 18:10:13 -0600
Update Date 2013-05-13 17:05:21 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name Dynorphin B
Description 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 (Wikipedia).
Structure Thumb
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  1. Prodynorphin 228-240
  2. Rimorphin
  3. Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Gln-Phe-Lys-Val-Val-Thr
Chemical Formula C74H115N21O17
Average Molecular Weight 1570.8354
Monoisotopic Molecular Weight 1569.877981359
IUPAC Name Not Available
Traditional IUPAC Name Not Available
CAS Registry Number 85006-82-2
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
InChI Identifier 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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • Alpha Amino Acid Or Derivative
  • Amphetamine Or Derivative
  • Beta Hydroxy Acid
  • Carboxamide Group
  • Carboxylic Acid Salt
  • Guanidine
  • N Acyl Alpha Amino Acid
  • N Acyl Amine
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Primary Carboxylic Acid Amide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Peptides
Status Expected and Not Quantified
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.013 g/L ALOGPS
LogP -1.29 ALOGPS
LogP -7.6 ChemAxon
LogS -5.08 ALOGPS
pKa (strongest acidic) 3.29 ChemAxon
pKa (strongest basic) 11.16 ChemAxon
Hydrogen Acceptor Count 25 ChemAxon
Hydrogen Donor Count 22 ChemAxon
Polar Surface Area 650.89 A2 ChemAxon
Rotatable Bond Count 51 ChemAxon
Refractivity 408.73 ChemAxon
Polarizability 166.36 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 3 ChemAxon
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029218
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Dynorphin_B Link_out
NuGOwiki Link HMDB12938 Link_out
Metagene Link HMDB12938 Link_out
METLIN ID Not Available
PubChem Compound 53481558 Link_out
PDB ID Not Available
ChEBI ID Not Available
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available