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Dynorphin A

CAT: 0804-HY-P1333-03Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-P1333-03Size:10 mg
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Description
Dynorphin A is an endogenous opioid peptide involved in inhibitory neurotransmission in the central nervous system (CNS) . Dynorphin A is a highy potent kappa opioid receptor (KOR) agonist, and is also an agonist for other opioid receptors, such as mu (MOR) and delta (DOR) . Dynorphin A can induce neuronal death, and can be used in the research of neurological disease[1][2].
CAS Number
80448-90-4
UNSPSC
12352209
Target
Apoptosis; Caspase; Endogenous Metabolite; Opioid Receptor
Type
Peptides
Related Pathways
Apoptosis; GPCR/G Protein; Metabolic Enzyme/Protease; Neuronal Signaling
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/dynorphin-a.html
Purity
96.21
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : ≥ 100 mg/mL
Smiles
O=C([C@H]1N(CCC1)C([C@H](CCCNC(N)=N)NC([C@H]([C@@H](C)CC)NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CC(C)C)NC([C@@H](NC(CNC(CNC([C@@H](N)CC2=CC=C(C=C2)O)=O)=O)=O)CC3=CC=CC=C3)=O)=O)=O)=O)=O)=O)N[C@@H](CCCCN)C(N[C@@H](CC(C)C)C(N[C@@H](CCCCN)C(N[C@H](C(N[C@@H](CC(O)=O)C(N[C@@H](CC(N)=O)C(N[C@H](C(O)=O)CCC(N)=O)=O)=O)=O)CC4=CNC5=CC=CC=C45)=O)=O)=O
Molecular Formula
C99H155N31O23
Molecular Weight
2147.48
References & Citations
[1]Zhang, et al.Dynorphin A as a Potential Endogenous Ligand for Four Members of the Opioid Receptor Gene Family. J Pharmacol Exp Ther. 1998 Jul;286 (1) :136-41.|[2]Aruna Sharma, et al. Monoclonal antibodies as novel neurotherapeutic agents in CNS injury and repair. Int Rev Neurobiol. 2012;102:23-45. |[3]I. N. SINGH, et al. Dynorphin A (1–17) induces apoptosis in striatal neurons in vitro through AMPA/kainate receptor-mediated cytochrome c release and caspase-3 activation. Neuroscience. 2003;122 (4) :1013-23. |[4]K F Hauser, et al. Dynorphin A (1-13) neurotoxicity in vitro: opioid and non-opioid mechanisms in mouse spinal cord neurons. Exp Neurol. 1999 Dec;160 (2) :361-75. |[5]B J Van de Heijning, et al. Dynorphin-A and vasopressin release in the rat: a structure-activity study. Neuropeptides. 1994 Jun;26 (6) :371-8. |[6]Takayoshi Mamiya, et al. Dynorphin a (1-13) alleviated stress-induced behavioral impairments in mice. Biol Pharm Bull. 2014;37 (8) :1269-73.
Shipping Conditions
Blue Ice
Storage Conditions
-80°C, 2 years; -20°C, 1 year (Powder, sealed storage, away from moisture and light)
Scientific Category
Peptides
Clinical Information
Phase 2
Isoform
Caspase 3; Human Endogenous Metabolite; κ Opioid Receptor/KOR

Chemical Information

Dynorphin A (swine)

Dynorphin is under investigation in clinical trial NCT00000244 (Effects of Dynorphin 1-13 on Heroin Addiction - 1).

CAS Number80448-90-4
PubChem CID16133805
IUPAC Name(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-carboxypropanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoic acid
Molecular FormulaC99H155N31O23
Molecular Weight2147.5
XLogP-7.8
Topological Polar Surface Area917
Hydrogen Bond Donor Count33
Hydrogen Bond Acceptor Count29
Rotatable Bond Count74
Heavy Atom Count153
Formal Charge0
Complexity4600
SMILES
CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)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)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)CNC(=O)CNC(=O)[C@H](CC5=CC=C(C=C5)O)N
InChI
InChI=1S/C99H155N31O23/c1-7-55(6)81(129-86(142)66(28-18-40-112-98(107)108)118-83(139)65(27-17-39-111-97(105)106)120-88(144)70(44-54(4)5)125-89(145)71(46-56-21-9-8-10-22-56)117-79(135)52-115-78(134)51-116-82(138)61(102)45-57-31-33-59(131)34-32-57)94(150)122-67(29-19-41-113-99(109)110)95(151)130-42-20-30-75(130)93(149)121-64(26-14-16-38-101)85(141)124-69(43-53(2)3)87(143)119-63(25-13-15-37-100)84(140)126-72(47-58-50-114-62-24-12-11-23-60(58)62)90(146)128-74(49-80(136)137)92(148)127-73(48-77(104)133)91(147)123-68(96(152)153)35-36-76(103)132/h8-12,21-24,31-34,50,53-55,61,63-75,81,114,131H,7,13-20,25-30,35-49,51-52,100-102H2,1-6H3,(H2,103,132)(H2,104,133)(H,115,134)(H,116,138)(H,117,135)(H,118,139)(H,119,143)(H,120,144)(H,121,149)(H,122,150)(H,123,147)(H,124,141)(H,125,145)(H,126,140)(H,127,148)(H,128,146)(H,129,142)(H,136,137)(H,152,153)(H4,105,106,111)(H4,107,108,112)(H4,109,110,113)/t55-,61-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,81-/m0/s1
InChIKey
JMNJYGMAUMANNW-FIXZTSJVSA-N
Chemical Structure
2D Structure
2D structure of Dynorphin A (swine)
CAS: 80448-90-4
CID: 16133805
Formula: C99H155N31O23
MW: 2147.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight2147.5
XLogP3-7.8
Hydrogen Bond Donor Count33
Hydrogen Bond Acceptor Count29
Rotatable Bond Count74
Exact Mass2147.1945652
Monoisotopic Mass2146.1912103
Topological Polar Surface Area917 Ų
Heavy Atom Count153
Formal Charge0
Complexity4600
Isotope Atom Count0
Defined Atom Stereocenter Count16
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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