Endomorphin

Endomorphin-2
Names
	IUPAC name (2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide
	Other names Tyr-Pro-Phe-Phe-NH2; L-Tyrosyl-L-prolyl-L-phenylalanyl-L-phenylalaninamide
Identifiers
CAS Number	141801-26-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL333357;
ChemSpider	4470615;
IUPHAR/BPS	3668;
PubChem CID	5311081;
UNII	3PH5M0466G;
	InChI InChI=1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1 Key: XIJHWXXXIMEHKW-LJWNLINESA-N;
	SMILES C1C[C@H](N(C1)C(=O)[C@H](CC2=CC=C(C=C2)O)N)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N;
Properties
Chemical formula	C32H37N5O5
Molar mass	571.678 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Endomorphin-1
Names
	IUPAC name (2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]-N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
	Other names Tyr-Pro-Trp-Phe-NH2; L-Tyrosyl-L-prolyl-L-tryptophyl-L-phenylalaninamide
Identifiers
CAS Number	189388-22-5;
3D model (JSmol)	Interactive image;
Abbreviations	YPWF
ChEBI	CHEBI:177580;
ChEMBL	ChEMBL316446;
ChemSpider	4470614;
IUPHAR/BPS	1623;
PubChem CID	5311080;
	InChI InChI=1S/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1 Key: ZEXLJFNSKAHNFH-SYKYGTKKSA-N;
	SMILES C1C[C@H](N(C1)C(=O)[C@H](CC2=CC=C(C=C2)O)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@@H](CC5=CC=CC=C5)C(=O)N;
Properties
Chemical formula	C34H38N6O5
Molar mass	610.715 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Endomorphins are considered to be natural opioid neurotransmitters central to pain relief. The two known endomorphins, endomorphin-1 and endomorphin-2, are tetrapeptides, consisting of Tyr-Pro-Trp-Phe and Tyr-Pro-Phe-Phe amino acid sequences respectively. These sequences fold into tertiary structures with high specificity and affinity for the μ-opioid receptor, binding it exclusively and strongly. Bound μ-opioid receptors typically induce inhibitory effects on neuronal activity. Endomorphin-like immunoreactivity exists within the central and peripheral nervous systems, where endomorphin-1 appears to be concentrated in the brain and upper brainstem, and endomorphin-2 in the spinal cord and lower brainstem. Because endomorphins activate the μ-opioid receptor, which is the target receptor of morphine and its derivatives, endomorphins possess significant potential as analgesics with reduced side effects and risk of addiction.

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