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β-Neoendorphin

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β-Neoendorphin
Names

Other names Beta-Neoendorphin
Identifiers
CAS Number	77739-21-0
3D model (JSmol)	Interactive image
ChemSpider	109029
IUPHAR/BPS	1644
PubChem CID	122260
CompTox Dashboard(EPA)	DTXSID401029639
InChI InChI=1S/C54H77N13O12/c1-32(2)26-41(65-51(76)42(28-33-10-4-3-5-11-33)62-46(71)31-60-45(70)30-61-47(72)38(56)27-34-15-19-36(68)20-16-34)50(75)64-40(13-8-24-59-54(57)58)48(73)63-39(12-6-7-23-55)49(74)66-43(29-35-17-21-37(69)22-18-35)52(77)67-25-9-14-44(67)53(78)79/h3-5,10-11,15-22,32,38-44,68-69H,6-9,12-14,23-31,55-56H2,1-2H3,(H,60,70)(H,61,72)(H,62,71)(H,63,73)(H,64,75)(H,65,76)(H,66,74)(H,78,79)(H4,57,58,59)/t38-,39-,40-,41-,42-,43-,44-/m0/s1 Key: RTXIYIQLESPXIV-VLOLPVCOSA-N InChI=1/C54H77N13O12/c1-32(2)26-41(65-51(76)42(28-33-10-4-3-5-11-33)62-46(71)31-60-45(70)30-61-47(72)38(56)27-34-15-19-36(68)20-16-34)50(75)64-40(13-8-24-59-54(57)58)48(73)63-39(12-6-7-23-55)49(74)66-43(29-35-17-21-37(69)22-18-35)52(77)67-25-9-14-44(67)53(78)79/h3-5,10-11,15-22,32,38-44,68-69H,6-9,12-14,23-31,55-56H2,1-2H3,(H,60,70)(H,61,72)(H,62,71)(H,63,73)(H,64,75)(H,65,76)(H,66,74)(H,78,79)(H4,57,58,59)/t38-,39-,40-,41-,42-,43-,44-/m0/s1 Key: RTXIYIQLESPXIV-VLOLPVCOBE
SMILES N[C@@H](CC1=CC=C(O)C=C1)C(NCC(NCC(N[C@@H](CC2=CC=CC=C2)C(N[C@@H](CC(C)C)C(N[C@@H](CCCNC(N)=N)C(N[C@@H](CCCCN)C(N[C@@H](CC3=CC=C(O)C=C3)C(N4CCC[C@H]4C(O)=O)=O)=O)=O)=O)=O)=O)=O)=O
Properties
Chemical formula	C₅₄H₇₇N₁₃O₁₂
Molar mass	1100.289 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

β-Neoendorphin is anendogenous opioid peptide with anonapeptide structure and theamino acid sequence Tyr-Gly-Gly-Phe-Leu-Arg-Lys-Tyr-Pro (YGGFLRKYP).^[1]

β-Neoendorphins (β-NEP) have the capability to stimulate wound healing by acceleratingkeratinocyte migration. This is achieved by β-NEP's activation ofmitogen-activated protein kinase (MAPK) andextracellular signal-regulated kinases 1 and 2 (ERK 1 and ERK 2); along with the upregulation of matrix metalloproteinase 2 and 9 (MMP-2 andMMP-9). Wound healing by β-NEP results in migration without consequences on proliferation in human keratinocytes.^[2]

References

[edit]

^Minamino N.; Kangawa K.; Chino N. (1981). "β-Neo-endorphin, a new hypothalamic 'big' leu-enkephalin of porcine origin: Its purification and the complete amino acid sequence".Biochemical and Biophysical Research Communications.99 (3):864–870.doi:10.1016/0006-291X(81)91243-2.PMID 7247945.
^Yang, Dong Joo; Moh, Sang Hyun; Choi, Yun-Hee; Kim, Ki Woo (2020-10-12)."β-Neoendorphin Enhances Wound Healing by Promoting Cell Migration in Keratinocyte".Molecules.25 (20): 4640.doi:10.3390/molecules25204640.ISSN 1420-3049.PMC 7587199.PMID 33053781.

Peptides:neuropeptides

Hormones

seehormones

Opioid peptides

Dynorphins	Dynorphin A Dynorphin A_1–8 Dynorphin B Big dynorphin Leumorphin α-Neoendorphin β-Neoendorphin
Endomorphins	Endomorphin-1 Endomorphin-2
Endorphins	α-Endorphin β-Endorphin γ-Endorphin
Enkephalins	Met-enkephalin Leu-enkephalin
Others	Adrenorphin Amidorphin Hemorphin Hemorphin-4 Nociceptin Opiorphin Spinorphin Valorphin

Other
neuropeptides

Kinins	Bradykinins Tachykinins: mammal Substance P Neurokinin A Neurokinin B amphibian Kassinin Physalaemin
Neuromedins	B N S U
Orexins	A B
Other	Angiotensin Bombesin Calcitonin gene-related peptide Carnosine Cocaine- and amphetamine-regulated transcript Delta-sleep-inducing peptide FMRFamide Galanin Galanin-like peptide Gastrin-releasing peptide Ghrelin Neuropeptide AF Neuropeptide FF Neuropeptide SF Neuropeptide VF Neuropeptide S Neuropeptide Y Neurophysins Neurotensin Pancreatic polypeptide Pituitary adenylate cyclase-activating peptide RVD-Hpα VGF