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Human Metabolome Database Version 3.5

Showing metabocard for Dynorphin B (HMDB12938)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
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Record Information
Version	3.5
Creation Date	2009-07-24 18:10:13 -0600
Update Date	2013-05-13 17:05:21 -0600
HMDB ID	HMDB12938
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	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	Prodynorphin 228-240 Rimorphin 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
InChI Key	AGTSSZRZBSNTGQ-QHDWWRMQSA-N
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
Substituents	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
Ontology
Status	Expected and Not Quantified
Origin	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
Spectra
	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
External Links
DrugBank 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
NuGOwiki Link	HMDB12938
Metagene Link	HMDB12938
METLIN ID	Not Available
PubChem Compound	53481558
PDB ID	Not Available
ChEBI ID	Not Available
References
Synthesis Reference	Not Available
Material Safety Data Sheet (MSDS)	Not Available
General References	Not Available

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