Tynorphin - Misplaced Pages

Synthetic opioid chemical compound

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Pharmaceutical compound

Tynorphin
Clinical data

ATC code	None
Legal status
Legal status	In general: non-regulated
Identifiers
IUPAC name (2S)-2-amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoic acid
PubChem CID	9961318
ChemSpider	8136925
Chemical and physical data
Formula	C₃₅H₄₆N₆O₇
Molar mass	662.788 g·mol
3D model (JSmol)	Interactive image Interactive image
SMILES CC(C)(C(=O)N(C(C)C)C(=O)N(CC1=CC=C(C=C1)O)C(=O)N2CCC2C(=O)N(CC3=CNC4=CC=CC=C43)C(=O)O)N O=C(N(C(=O)N(C(=O)N1CCC1C(=O)N(C(=O)O)Cc3c2ccccc2c3)Cc4ccc(O)cc4)C(C)C)(N)C(C)C
InChI InChI=1S/C35H46N6O7/c1-19(2)29(36)32(44)40-30(20(3)4)33(45)38-26(16-21-11-13-23(42)14-12-21)34(46)41-15-7-10-28(41)31(43)39-27(35(47)48)17-22-18-37-25-9-6-5-8-24(22)25/h5-6,8-9,11-14,18-20,26-30,37,42H,7,10,15-17,36H2,1-4H3,(H,38,45)(H,39,43)(H,40,44)(H,47,48)/t26-,27-,28-,29-,30-/m0/s1 Key:WLWBANYDSJWZBI-IIZANFQQSA-N

Tynorphin is a synthetic opioid peptide which is a potent and competitive inhibitor of the enkephalinase class of enzymes which break down the endogenous enkephalin peptides. It specifically inactivates dipeptidyl aminopeptidase III (DPP3) with very high efficacy, but also inhibits neutral endopeptidase (NEP), aminopeptidase N (APN), and angiotensin-converting enzyme (ACE) to a lesser extent. It has a pentapeptide structure with the amino acid sequence Val-Val-Tyr-Pro-Trp (VVYPW).

Tynorphin was discovered in an attempt to develop an enkephalinase inhibitor of greater potency than spinorphin.

References

^ Yamamoto Y, Hashimoto J, Shimamura M, Yamaguchi T, Hazato T (April 2000). "Characterization of tynorphin, a potent endogenous inhibitor of dipeptidyl peptidaseIII". Peptides. 21 (4): 503–8. doi:10.1016/S0196-9781(00)00174-1. PMID 10822105. S2CID 30916029.