Spinorphin

Spinorphin
Names
	IUPAC name L-leucyl-L-valyl-L-valyl-L-tyrosyl-L-prolyl-L-tryptophyl-L-threonine
	Other names LVVYPWT; LVV-hemorphin-4
Identifiers
CAS Number	137201-62-8
ChemSpider	2339355
IUPHAR/BPS	1026
Jmol 3D model	Interactive image
PubChem	3081832
	InChI InChI=1S/C45H64N8O10/c1-23(2)19-31(46)39(56)50-37(25(5)6)43(60)51-36(24(3)4)42(59)49-34(20-27-14-16-29(55)17-15-27)44(61)53-18-10-13-35(53)41(58)48-33(40(57)52-38(26(7)54)45(62)63)21-28-22-47-32-12-9-8-11-30(28)32/h8-9,11-12,14-17,22-26,31,33-38,47,54-55H,10,13,18-21,46H2,1-7H3,(H,48,58)(H,49,59)(H,50,56)(H,51,60)(H,52,57)(H,62,63)/t26-,31+,33+,34+,35+,36+,37+,38+/m1/s1 Key: BXIFNVGZIMFBQB-DYDSHOKNSA-N ; InChI=1/C45H64N8O10/c1-23(2)19-31(46)39(56)50-37(25(5)6)43(60)51-36(24(3)4)42(59)49-34(20-27-14-16-29(55)17-15-27)44(61)53-18-10-13-35(53)41(58)48-33(40(57)52-38(26(7)54)45(62)63)21-28-22-47-32-12-9-8-11-30(28)32/h8-9,11-12,14-17,22-26,31,33-38,47,54-55H,10,13,18-21,46H2,1-7H3,(H,48,58)(H,49,59)(H,50,56)(H,51,60)(H,52,57)(H,62,63)/t26-,31+,33+,34+,35+,36+,37+,38+/m1/s1 Key: BXIFNVGZIMFBQB-DYDSHOKNBN ;
	SMILES O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)O)[C@H](O)C)Cc3c2ccccc2[nH]c3)Cc4ccc(O)cc4)C(C)C)C(C)C)[C@@H](N)CC(C)C ;
Properties
Chemical formula	C45H64N8O10
Molar mass	877.037 g/mol
Vapor pressure	{{{value}}}
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Spinorphin is an endogenous, non-classical opioid peptide of the hemorphin family^[1] first isolated from the bovine spinal cord (hence the prefix spin-)^[2] and acts as a regulator of the enkephalinases, a class of enzymes that break down endogenous the enkephalin peptides.^[3] It does so by inhibiting the enzymes aminopeptidase N (APN), dipeptidyl peptidase III (DPP3), angiotensin-converting enzyme (ACE), and neutral endopeptidase (NEP).^[3] Spinorphin is a heptapeptide and has the amino acid sequence Leu-Val-Val-Tyr-Pro-Trp-Thr (LVVYPWT).^[3] It has been observed to possess antinociceptive,^[4] antiallodynic,^[4] and anti-inflammatory properties.^[1] The mechanism of action of spinorphin has not been fully elucidated (i.e., how it acts to inhibit the enkephalinases), but it has been found to act as an antagonist of the P2X₃ receptor,^[5] and as a weak partial agonist/antagonist of the FP₁ receptor.^[1]

References

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