Valorphin

Valorphin, also known as VV-hemorphin-5, is a naturally occurring, endogenous opioid heptapeptide of the hemorphin family with the amino acid sequence H-Val-Val-Tyr-Pro-Trp-Thr-Gln-OH (VVYPWTQ).^[1][2][3] It is produced in the body via proteolyic cleavage of residues 33-39 of the β-chain of hemoglobin.^[2][4] Valorphin binds preferentially to the μ-opioid receptor and produces effects such as analgesia and self-administration in animals.^[1][2] It also possesses cytotoxic and antiproliferative properties against tumor cells,^[3][4][5][6] the mediation of which, because they are reversed by naloxone, appears to be dependent on the opioid receptors.^[5]

Quick facts Names, Identifiers ...

Valorphin

Names
IUPAC name L-Valyl-L-valyl-L-tyrosyl-L-prolyl-L-tryptophyl-L-threonyl-L-glutamine
Identifiers
CAS Number	144313-54-2 N[ChemSpider]
3D model (JSmol)	Interactive image
ChemSpider	27470960
PubChem CID	90470048
InChI InChI=1S/C44H60N8O12/c1-22(2)35(45)40(59)50-36(23(3)4)41(60)49-32(19-25-12-14-27(54)15-13-25)43(62)52-18-8-11-33(52)39(58)48-31(20-26-21-46-29-10-7-6-9-28(26)29)38(57)51-37(24(5)53)42(61)47-30(44(63)64)16-17-34(55)56/h6-7,9-10,12-15,21-24,30-33,35-37,46,53-54H,8,11,16-20,45H2,1-5H3,(H,47,61)(H,48,58)(H,49,60)(H,50,59)(H,51,57)(H,55,56)(H,63,64)/t24-,30+,31+,32+,33+,35+,36+,37+/m1/s1 Key: CNYWVXYFCKFXLL-NMUVPRMFSA-N
SMILES C[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H]3CCCN3C(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N)O
Properties
Chemical formula	C44H61N9O11
Molar mass	892.024 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

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