Tynorphin

Tynorphin
Clinical data
ATC code	None;
Legal status
Legal status	In general: non-regulated;
Identifiers
	IUPAC name (2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]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−1
3D model (JSmol)	Interactive image; Interactive image;
	SMILES CC(C)[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)O)N; ; O=C(N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)O)Cc3c2ccccc2[nH]c3)Cc4ccc(O)cc4)C(C)C)[C@@H](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.^[1] 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.^[1] 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.^[1]

References

^ ^a ^b ^c 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.

Clinical data

ATC code	None
Legal status
Legal status	In general: non-regulated
Identifiers
IUPAC name (2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]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⁻¹
3D model (JSmol)	Interactive image Interactive image
SMILES CC(C)[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)O)N O=C(N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)O)Cc3c2ccccc2[nH]c3)Cc4ccc(O)cc4)C(C)C)[C@@H](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