β-Endorphin

β-Endorphin
Names
IUPAC name
L-Tyrosylglycylglycyl-L-phenylalanyl-L-methionyl-L-threonyl-L-seryl-L-glutaminyl-L-lysyl-L-seryl-L-glutaminyl-L-threonyl-L-prolyl-L-leucyl-L-valyl-L-threonyl-L-leucyl-L-phenylalanyl-L-lysyl-L-asparaginyl-L-alanyl-L-isoleucyl-L-isoleucyl-L-lysyl-L-asparaginyl-L-alanyl-L-tyrosyl-L-lysyl-L-lysylglycyl-L-glutamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.056.646
PubChem CID
UNII
InChI
  • InChI=1S/C158H253N41O44S/c1-17-84(9)126(153(237)184-102(44-29-34-65-163)137(221)188-112(74-120(168)210)142(226)173-86(11)131(215)185-110(73-94-48-52-96(206)53-49-94)146(230)179-99(41-26-31-62-160)135(219)177-98(40-25-30-61-159)134(218)172-78-124(214)175-106(158(242)243)56-59-119(167)209)195-154(238)127(85(10)18-2)194-132(216)87(12)174-143(227)113(75-121(169)211)187-136(220)100(42-27-32-63-161)180-147(231)111(72-92-38-23-20-24-39-92)186-144(228)107(68-81(3)4)190-155(239)129(89(14)203)197-152(236)125(83(7)8)193-148(232)108(69-82(5)6)189-151(235)116-45-35-66-199(116)157(241)130(90(15)204)198-140(224)104(55-58-118(166)208)182-149(233)114(79-200)191-138(222)101(43-28-33-64-162)178-139(223)103(54-57-117(165)207)181-150(234)115(80-201)192-156(240)128(88(13)202)196-141(225)105(60-67-244-16)183-145(229)109(71-91-36-21-19-22-37-91)176-123(213)77-170-122(212)76-171-133(217)97(164)70-93-46-50-95(205)51-47-93/h19-24,36-39,46-53,81-90,97-116,125-130,200-206H,17-18,25-35,40-45,54-80,159-164H2,1-16H3,(H2,165,207)(H2,166,208)(H2,167,209)(H2,168,210)(H2,169,211)(H,170,212)(H,171,217)(H,172,218)(H,173,226)(H,174,227)(H,175,214)(H,176,213)(H,177,219)(H,178,223)(H,179,230)(H,180,231)(H,181,234)(H,182,233)(H,183,229)(H,184,237)(H,185,215)(H,186,228)(H,187,220)(H,188,221)(H,189,235)(H,190,239)(H,191,222)(H,192,240)(H,193,232)(H,194,216)(H,195,238)(H,196,225)(H,197,236)(H,198,224)(H,242,243)/t84-,85-,86-,87-,88+,89+,90+,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,125-,126-,127-,128-,129-,130-/m0/s1
    Key: WOPZMFQRCBYPJU-NTXHZHDSSA-N
  • InChI=1/C158H253N41O44S/c1-17-84(9)126(153(237)184-102(44-29-34-65-163)137(221)188-112(74-120(168)210)142(226)173-86(11)131(215)185-110(73-94-48-52-96(206)53-49-94)146(230)179-99(41-26-31-62-160)135(219)177-98(40-25-30-61-159)134(218)172-78-124(214)175-106(158(242)243)56-59-119(167)209)195-154(238)127(85(10)18-2)194-132(216)87(12)174-143(227)113(75-121(169)211)187-136(220)100(42-27-32-63-161)180-147(231)111(72-92-38-23-20-24-39-92)186-144(228)107(68-81(3)4)190-155(239)129(89(14)203)197-152(236)125(83(7)8)193-148(232)108(69-82(5)6)189-151(235)116-45-35-66-199(116)157(241)130(90(15)204)198-140(224)104(55-58-118(166)208)182-149(233)114(79-200)191-138(222)101(43-28-33-64-162)178-139(223)103(54-57-117(165)207)181-150(234)115(80-201)192-156(240)128(88(13)202)196-141(225)105(60-67-244-16)183-145(229)109(71-91-36-21-19-22-37-91)176-123(213)77-170-122(212)76-171-133(217)97(164)70-93-46-50-95(205)51-47-93/h19-24,36-39,46-53,81-90,97-116,125-130,200-206H,17-18,25-35,40-45,54-80,159-164H2,1-16H3,(H2,165,207)(H2,166,208)(H2,167,209)(H2,168,210)(H2,169,211)(H,170,212)(H,171,217)(H,172,218)(H,173,226)(H,174,227)(H,175,214)(H,176,213)(H,177,219)(H,178,223)(H,179,230)(H,180,231)(H,181,234)(H,182,233)(H,183,229)(H,184,237)(H,185,215)(H,186,228)(H,187,220)(H,188,221)(H,189,235)(H,190,239)(H,191,222)(H,192,240)(H,193,232)(H,194,216)(H,195,238)(H,196,225)(H,197,236)(H,198,224)(H,242,243)/t84-,85-,86-,87-,88+,89+,90+,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,125-,126-,127-,128-,129-,130-/m0/s1
    Key: WOPZMFQRCBYPJU-NTXHZHDSBY
SMILES
  • CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]3CCCN3C(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc4ccccc4)NC(=O)CNC(=O)CNC(=O)[C@H](Cc5ccc(cc5)O)N
Properties
Chemical formula
C158H251N39O46S
Molar mass 3465.03 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

β-Endorphin (beta-endorphin) is an endogenous opioid neuropeptide and peptide hormone that is produced in certain neurons within the central nervous system and peripheral nervous system.[1] It is one of three endorphins that are produced in humans, the others being α-endorphin and γ-endorphin.[2]

There are multiple forms of β-endorphins with the full sequence of Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu (31 amino acids) denoted as β-endorphin(1-31) and variants truncated to the first 26 and 27 amino acids as β-endorphin(1-26) and β-endorphin(1-27). [1][3][4] However, β-endorphin(1-31) is the only form that possess a potent analgesic effect and it is the primary form located in the anterior pituitary gland, and regions such as the hypothalamus, midbrain, and amygdala.[5] The first 16 amino acids are identical to α-endorphin. β-Endorphin is considered to be a part of the endogenous opioid and endorphin classes of neuropeptides;[1] all of the established endogenous opioid peptides contain the same N-terminal amino acid sequence, Tyr-Gly-Gly-Phe, followed by either -Met or -Leu.[1]

Function of β-endorphin has been known to be associated with hunger, thrill, pain, maternal care, sexual behavior, and reward cognition. In the broadest sense, β-endorphin is primarily utilized in the body to reduce stress and maintain homeostasis. In behavioral research, studies have shown that β-endorphin is released via volume transmission into the ventricular system in response to a variety of stimuli, and novel stimuli in particular.[6]

  1. ^ a b c d Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 7: Neuropeptides". In Sydor A, Brown RY (eds.). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). New York: McGraw-Hill Medical. pp. 184, 190, 192. ISBN 978-0-07-148127-4. Opioid Peptides
    β-Endorphin (also a pituitary hormone) ...
    Opioid peptides are encoded by three distinct genes. These precursors include POMC, from which the opioid peptide β-endorphin and several nonopioid peptides are derived, as discussed earlier; proenkephalin, from which met-enkephalin and leu-enkephalin are derived; and prodynorphin, which is the precursor of dynorphin and related peptides. Although they come from different precursors, opioid peptides share significant amino acid sequence identity. Specifically, all of the well-validated endogenous opioids contain the same four N-terminal amino acids (Tyr-Gly-Gly-Phe), followed by either Met or Leu ... Among endogenous opioid peptides, β-endorphin binds preferentially to μ receptors. ... Shared opioid peptide sequences. Although they vary in length from as few as five amino acids (enkephalins) to as many as 31 (β-endorphin), the endogenous opioid peptides shown here contain a shared N-terminal sequence followed by either Met or Leu.
  2. ^ Li Y, Lefever MR, Muthu D, Bidlack JM, Bilsky EJ, Polt R (February 2012). "Opioid glycopeptide analgesics derived from endogenous enkephalins and endorphins". Future Medicinal Chemistry. 4 (2). Table 1: Endogenous opioid peptides. doi:10.4155/fmc.11.195. PMC 3306179. PMID 22300099.
  3. ^ Pilozzi A, Carro C, Huang X (December 2020). "Roles of β-Endorphin in Stress, Behavior, Neuroinflammation, and Brain Energy Metabolism". International Journal of Molecular Sciences. 22 (1): 338. doi:10.3390/ijms22010338. PMC 7796446. PMID 33396962.
  4. ^ DBGET
  5. ^ Pilozzi A, Carro C, Huang X (30 December 2020). "Roles of β-endorphin in stress, behavior, neuroinflammation, and brain energy metabolism". International Journal of Molecular Sciences. 22 (1): 338. doi:10.3390/ijms22010338. PMC 7796446. PMID 33396962.
  6. ^ Veening JG, Barendregt HP (January 2015). "The effects of beta-endorphin: state change modification". Fluids and Barriers of the CNS. 12: 3. doi:10.1186/2045-8118-12-3. PMC 4429837. PMID 25879522.