Hemorphin-4

Hemorphin-4
Names
	IUPAC name (2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxybutanoic acid
	Other names L-tyrosyl-L-prolyl-L-tryptophyl-L-threonine
Identifiers
CAS Number	103930-64-9;
3D model (JSmol)	Interactive image;
ChemSpider	16725618;
PubChem CID	128444;
CompTox Dashboard (EPA)	DTXSID20908670 ;
	InChI InChI=1S/C29H35N5O7/c1-16(35)25(29(40)41)33-26(37)23(14-18-15-31-22-6-3-2-5-20(18)22)32-27(38)24-7-4-12-34(24)28(39)21(30)13-17-8-10-19(36)11-9-17/h2-3,5-6,8-11,15-16,21,23-25,31,35-36H,4,7,12-14,30H2,1H3,(H,32,38)(H,33,37)(H,40,41)/t16-,21+,23+,24+,25+/m1/s1 Key: WEGGKZQIJMQCGR-RECQUVTISA-N;
	SMILES C[C@H]([C@@H](C(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H]3CCCN3C(=O)[C@H](Cc4ccc(cc4)O)N)O;
Properties
Chemical formula	C29H35N5O7
Molar mass	565.618 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hemorphin-4 is an endogenous opioid peptide of the hemorphin family which possesses antinociceptive properties and is derived from the β-chain of hemoglobin in the bloodstream.^[1]^[2] It is a tetrapeptide with the amino acid sequence Tyr-Pro-Trp-Thr. Hemorphin-4 has affinities for the μ-, δ-, and κ-opioid receptors that are in the same range as the structurally related β-casomorphins, although affinity to the κ-opioid receptor is markedly higher in comparison.^[3] It acts as an agonist at these sites.^[4] Hemorphin-4 also has inhibitory effects on angiotensin-converting enzyme (ACE),^[5] and as a result, may play a role in the regulation of blood pressure.^[3] Notably, inhibition of ACE also reduces enkephalin catabolism.^[6]

References

^ Brantl V, Gramsch C, Lottspeich F, Mertz R, Jaeger KH, Herz A (June 1986). "Novel opioid peptides derived from hemoglobin: hemorphins". European Journal of Pharmacology. 125 (2): 309–10. doi:10.1016/0014-2999(86)90044-0. PMID 3743640.
^ Davis TP, Gillespie TJ, Porreca F (1989). "Peptide fragments derived from the beta-chain of hemoglobin (hemorphins) are centrally active in vivo". Peptides. 10 (4): 747–51. doi:10.1016/0196-9781(89)90107-1. PMID 2587417. S2CID 11168006.
^ ^a ^b Liebmann C, Schrader U, Brantl V (August 1989). "Opioid receptor affinities of the blood-derived tetrapeptides hemorphin and cytochrophin". European Journal of Pharmacology. 166 (3): 523–6. doi:10.1016/0014-2999(89)90368-3. PMID 2553436.
^ Erchegyi J, Kastin AJ, Zadina JE (1992). "Isolation of a novel tetrapeptide with opiate and antiopiate activity from human brain cortex: Tyr-Pro-Trp-Gly-NH2 (Tyr-W-MIF-1)". Peptides. 13 (4): 623–31. doi:10.1016/0196-9781(92)90165-Y. PMID 1359507. S2CID 32330624.
^ Lantz I, Glämsta EL, Talbäck L, Nyberg F (August 1991). "Hemorphins derived from hemoglobin have an inhibitory action on angiotensin converting enzyme activity". FEBS Letters. 287 (1–2): 39–41. doi:10.1016/0014-5793(91)80011-Q. PMID 1652464. S2CID 26892050.
^ Benuck M, Berg MJ, Marks N (1982). "Separate metabolic pathways for Leu-enkephalin and Met-enkephalin-Arg(6)-Phe(7) degradation by rat striatal synaptosomal membranes". Neurochemistry International. 4 (5): 389–96. doi:10.1016/0197-0186(82)90081-X. PMID 20487892. S2CID 23138078.

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[pmid3743640-1] Brantl V, Gramsch C, Lottspeich F, Mertz R, Jaeger KH, Herz A (June 1986). "Novel opioid peptides derived from hemoglobin: hemorphins". European Journal of Pharmacology. 125 (2): 309–10. doi:10.1016/0014-2999(86)90044-0. PMID 3743640.

[pmid2587417-2] Davis TP, Gillespie TJ, Porreca F (1989). "Peptide fragments derived from the beta-chain of hemoglobin (hemorphins) are centrally active in vivo". Peptides. 10 (4): 747–51. doi:10.1016/0196-9781(89)90107-1. PMID 2587417. S2CID 11168006.

[pmid2553436-3] Liebmann C, Schrader U, Brantl V (August 1989). "Opioid receptor affinities of the blood-derived tetrapeptides hemorphin and cytochrophin". European Journal of Pharmacology. 166 (3): 523–6. doi:10.1016/0014-2999(89)90368-3. PMID 2553436.

[pmid1359507-4] Erchegyi J, Kastin AJ, Zadina JE (1992). "Isolation of a novel tetrapeptide with opiate and antiopiate activity from human brain cortex: Tyr-Pro-Trp-Gly-NH2 (Tyr-W-MIF-1)". Peptides. 13 (4): 623–31. doi:10.1016/0196-9781(92)90165-Y. PMID 1359507. S2CID 32330624.

[pmid1652464-5] Lantz I, Glämsta EL, Talbäck L, Nyberg F (August 1991). "Hemorphins derived from hemoglobin have an inhibitory action on angiotensin converting enzyme activity". FEBS Letters. 287 (1–2): 39–41. doi:10.1016/0014-5793(91)80011-Q. PMID 1652464. S2CID 26892050.

[pmid20487892-6] Benuck M, Berg MJ, Marks N (1982). "Separate metabolic pathways for Leu-enkephalin and Met-enkephalin-Arg(6)-Phe(7) degradation by rat striatal synaptosomal membranes". Neurochemistry International. 4 (5): 389–96. doi:10.1016/0197-0186(82)90081-X. PMID 20487892. S2CID 23138078.

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See also

References