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77614-16-5

77614-16-5 Structure

77614-16-5 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[WGK Germany ]

3
Questions And AnswerBack 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.
Hazard InformationBack 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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