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Showing Compound Dynorphin A 9-17 (FDB029214)

Record Information
Version1.0
Creation date2011-09-21 01:51:57 UTC
Update date2015-07-21 06:59:39 UTC
Primary IDFDB029214
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDynorphin A 9-17
DescriptionDynorphin A (9-17) is a fraction of Dynorphin A with only Arg-Pro-Lys-Leu-Lys-Trp-Asp-Asn-Gln peptide chain Dynorphin A is an endogenous opioid peptide that produces non-opioid receptor-mediated neural excitation.Dynorphin induces calcium influx via voltage-sensitive calcium channels in sensory neurons by activating bradykinin receptors. This action of dynorphin at bradykinin receptors is distinct from the primary signaling pathway activated by bradykinin and underlies the hyperalgesia produced by pharmacological administration of dynorphin by the spinal route in rats and mice. Blockade of spinal B1 or B2 receptor also reverses persistent neuropathic pain but only when there is sustained elevation of endogenous spinal dynorphin, which is required for maintenance of neuropathic pain. These data reveal a mechanism for endogenous dynorphin to promote pain through its agonist action at bradykinin receptors and suggest new avenues for therapeutic intervention. Dynorphin A 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]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP-2ALOGPS
logP-12ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)12.04ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area542.52 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity332.37 m³·mol⁻¹ChemAxon
Polarizability123.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC53H85N17O14
IUPAC name(2S)-2-[(2R)-2-[(2R)-2-[(2S)-2-[(2S)-6-amino-2-[(2R)-2-[(2R)-6-amino-2-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-4-methylpentanamido]hexanamido]-3-(1H-indol-3-yl)propanamido]-3-carboxypropanamido]-3-(C-hydroxycarbonimidoyl)propanamido]-4-(C-hydroxycarbonimidoyl)butanoic acid
InChI IdentifierInChI=1S/C53H85N17O14/c1-28(2)23-36(66-45(76)34(15-6-8-20-55)64-50(81)40-16-10-22-70(40)51(82)31(56)12-9-21-61-53(59)60)46(77)63-33(14-5-7-19-54)44(75)67-37(24-29-27-62-32-13-4-3-11-30(29)32)47(78)69-39(26-43(73)74)49(80)68-38(25-42(58)72)48(79)65-35(52(83)84)17-18-41(57)71/h3-4,11,13,27-28,31,33-40,62H,5-10,12,14-26,54-56H2,1-2H3,(H2,57,71)(H2,58,72)(H,63,77)(H,64,81)(H,65,79)(H,66,76)(H,67,75)(H,68,80)(H,69,78)(H,73,74)(H,83,84)(H4,59,60,61)/t31-,33-,34+,35-,36+,37-,38+,39+,40-/m0/s1
InChI KeyRBCKMCPFHXXHJN-CELVLHDCSA-N
Isomeric SMILESCC(C)C[C@@H](NC(=O)[C@@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=N)C(=O)N[C@@H](CCC(O)=N)C(O)=O
Average Molecular Weight1184.3475
Monoisotopic Molecular Weight1183.646190513
Classification
Description Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • 4-oxosteroid
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-1900000000-724e78d28e84b37a67d02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hk9-4921010101-6c664ea35ea87e7bad3d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0it9-9511000000-d4b3ae2476ff4af77f302017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03l3-3900000000-4c336fcd5ad5080e8b052017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-9800000101-cd94d0f87364dd9502ce2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9211100111-849d065074d0e31752d92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0900000000-62711c8b505fe0269c572021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4901100101-9da62822f4925861cdf82021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i0-7910001110-9b7411ebd27c058fe1c22021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900010000-b616cc3e3abb179fa8552021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007o-9800000100-3ec8802bc12ae72f25032021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7o-9601220460-4a6ab4ff4d87185f63222021-09-25View Spectrum
NMRNot Available
ChemSpider ID30776661
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481553
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12934
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference