| Identification | Back Directory | [Name]
DERMORPHIN ACETATE | [CAS]
77614-16-5 | [Synonyms]
DERMORPHIN
Dermorphin HAc
Dermorphin Powder
DERMORPHIN ACETATE
Dermorphin trifluoroacetate salt
L-Tyr-D-Ala-L-Phe-Gly-L-Tyr-L-Pro-L-Ser-NH2
Tyrosyl-alanyl-phenylalanyl-glycyl-tyrosyl-prolyl-serinamide
(2S)-1-[(2S)-2-[[2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenyl-propanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]-N-[(1S)-1-carbamoyl-2-hydro
(2S)-N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]-1-[(2S)-2-[[2-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxamide | [EINECS(EC#)]
202-853-6 | [Molecular Formula]
C40H50N8O10 | [MDL Number]
MFCD00076694 | [MOL File]
77614-16-5.mol | [Molecular Weight]
802.87 |
| Chemical Properties | Back Directory | [Melting point ]
157-159 °C | [Boiling point ]
1323.8±65.0 °C(Predicted) | [density ]
1.363±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO | [form ]
powder | [pka]
9.83±0.15(Predicted) | [color ]
white to off-white | [Sequence]
H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2 | [InChIKey]
FHZPGIUBXYVUOY-VWGYHWLBSA-N | [SMILES]
C(N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N)(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC1C=CC(O)=CC=1)CC1C=CC=CC=1)CC1C=CC(O)=CC=1 |
| Questions And Answer | Back Directory | [Structure]
Dermorphin does not contain the common N-terminal sequence for the traditional endogenous opioid peptides (Tyr–Gly–Gly–Phe), and its sequence is completely different from those of the endomorphins, which were identified as endogenous μ-opioid peptides that also do not contain the common sequence. Interestingly, DM contains D-alanine (a D-isomer amino acid) in its sequence. The primary structure of dermorphin is YDAFGYPS-NH2.
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| Hazard Information | Back Directory | [Description]
Dermorphin was first isolated from the skin of the skin of South American frogs of the genus Phyllomedusa. It is a high potency natural opiate peptide that binds selectively to mu-opioid receptors. | [Uses]
A mu-opioid receptor agonist | [Definition]
ChEBI: Dermorphin is an oligopeptide. | [Side effects]
Like μ-opiate agonists, dermorphins produce antinociception and also catalepsy, respiratory depression, constipation, tolerance, and dependence, although at a lower degree than morphine does[1].
| [in vitro]
Dermorphin, a peptide isolated from the skin of Phyllomedusa frogs and the peptide receptor (NOP) component by the endogenous agonist nociceptin/orphanin FQ (N/OFQ). In displacement binding studies at CHOhMu, Dermorphin and DeNo displac the binding of [3H]-DPN in a concentration dependent and saturable manner. Dermorphin displays an affinity of 7.17, while N/OFQ fails to displace [3H]-DPN at the Delta receptor. Dermorphin and DeNo stimulate the binding of GTPγ[35S] in a concentration dependent and saturable manner at the Mu receptor.
| [References]
[1] Negri, L. P. Melchiorri and R. Lattanzi. “Opioid and Bv8 Peptides.”Handbook of Biologically Active Peptides (Second Edition) 2013:376-383.
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