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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:10:13 UTC
Update Date2017-10-23 19:06:07 UTC
HMDB IDHMDB0012938
Secondary Accession Numbers
  • HMDB12938
Metabolite Identification
Common NameDynorphin B
DescriptionDynorphin 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
Synonyms
ValueSource
Prodynorphin 228-240HMDB
RimorphinHMDB
Tyr-gly-gly-phe-leu-arg-arg-GLN-phe-lys-val-val-THRHMDB
Chemical FormulaC74H115N21O17
Average Molecular Weight1570.8354
Monoisotopic Molecular Weight1569.877981359
IUPAC Name(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
Traditional Name(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
CAS Registry Number85006-82-2
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 KeyAGTSSZRZBSNTGQ-QHDWWRMQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic Polymers
Sub ClassPolypeptides
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Alpha peptide
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Glutamine or derivatives
  • Leucine or derivatives
  • N-acyl-alpha-amino acid
  • Valine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty amide
  • Hydroxy acid
  • N-acyl-amine
  • Fatty acyl
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid
  • Primary carboxylic acid amide
  • Carboxamide group
  • Guanidine
  • Carboximidamide
  • Organic 1,3-dipolar compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Alcohol
  • Organic oxygen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP-1.3ALOGPS
logP-7.6ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)11.16ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count22ChemAxon
Polar Surface Area650.89 ŲChemAxon
Rotatable Bond Count51ChemAxon
Refractivity408.73 m³·mol⁻¹ChemAxon
Polarizability166.36 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udu-0941050000-c591c899867f3644c716View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-2923110000-30e095ba11471355f59cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-1920000000-1498e209cade6559c9f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-1000290000-2fceae46bb2e62ca462bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-2111490000-a27e994b010ed083f8c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r7-8363942142-cb5ed65bf775fe65c639View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029218
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDynorphin_B
METLIN IDNot Available
PubChem Compound53481558
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available