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{{Chembox |
{{Chembox |
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| verifiedrevid = |
| verifiedrevid = 447369158 |
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| ImageFile = Amidorphin. |
| ImageFile = Amidorphin.svg |
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| ImageSize = 200px |
| ImageSize = 200px |
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| IUPACName = |
| IUPACName = |
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| OtherNames = |
| OtherNames = |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 94885-44-6 |
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| CASNo = 94885-44-6 |
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| PubChem = 16132380 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 17289039 |
| ChemSpiderID = 17289039 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C131H200N30O43S2/c1-66(2)54-88(110(136)183)153-130(203)109(70(9)10)159-122(195)80(35-41-101(169)170)142-99(167)64-137-98(166)63-140-113(186)92(60-96(135)164)154-111(184)71(11)141-114(187)81(36-42-102(171)172)146-117(190)82(37-43-103(173)174)147-118(191)84(39-45-105(177)178)152-129(202)108(69(7)8)160-123(196)85(40-46-106(179)180)149-124(197)90(56-68(5)6)157-128(201)95-26-21-51-161(95)131(204)94(59-74-29-33-76(163)34-30-74)158-125(198)89(55-67(3)4)155-119(192)83(38-44-104(175)176)148-127(200)93(61-107(181)182)156-121(194)87(48-53-206-13)150-116(189)79(25-18-20-50-133)144-115(188)78(24-17-19-49-132)145-120(193)86(47-52-205-12)151-126(199)91(58-72-22-15-14-16-23-72)143-100(168)65-138-97(165)62-139-112(185)77(134)57-73-27-31-75(162)32-28-73/h14-16,22-23,27-34,66-71,77-95,108-109,162-163H,17-21,24-26,35-65,132-134H2,1-13H3,(H2,135,164)(H2,136,183)(H,137,166)(H,138,165)(H,139,185)(H,140,186)(H,141,187)(H,142,167)(H,143,168)(H,144,188)(H,145,193)(H,146,190)(H,147,191)(H,148,200)(H,149,197)(H,150,189)(H,151,199)(H,152,202)(H,153,203)(H,154,184)(H,155,192)(H,156,194)(H,157,201)(H,158,198)(H,159,195)(H,160,196)(H,169,170)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H,179,180)(H,181,182)/t71-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,108-,109-/m0/s1 |
| StdInChI = 1S/C131H200N30O43S2/c1-66(2)54-88(110(136)183)153-130(203)109(70(9)10)159-122(195)80(35-41-101(169)170)142-99(167)64-137-98(166)63-140-113(186)92(60-96(135)164)154-111(184)71(11)141-114(187)81(36-42-102(171)172)146-117(190)82(37-43-103(173)174)147-118(191)84(39-45-105(177)178)152-129(202)108(69(7)8)160-123(196)85(40-46-106(179)180)149-124(197)90(56-68(5)6)157-128(201)95-26-21-51-161(95)131(204)94(59-74-29-33-76(163)34-30-74)158-125(198)89(55-67(3)4)155-119(192)83(38-44-104(175)176)148-127(200)93(61-107(181)182)156-121(194)87(48-53-206-13)150-116(189)79(25-18-20-50-133)144-115(188)78(24-17-19-49-132)145-120(193)86(47-52-205-12)151-126(199)91(58-72-22-15-14-16-23-72)143-100(168)65-138-97(165)62-139-112(185)77(134)57-73-27-31-75(162)32-28-73/h14-16,22-23,27-34,66-71,77-95,108-109,162-163H,17-21,24-26,35-65,132-134H2,1-13H3,(H2,135,164)(H2,136,183)(H,137,166)(H,138,165)(H,139,185)(H,140,186)(H,141,187)(H,142,167)(H,143,168)(H,144,188)(H,145,193)(H,146,190)(H,147,191)(H,148,200)(H,149,197)(H,150,189)(H,151,199)(H,152,202)(H,153,203)(H,154,184)(H,155,192)(H,156,194)(H,157,201)(H,158,198)(H,159,195)(H,160,196)(H,169,170)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H,179,180)(H,181,182)/t71-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,108-,109-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BRCPMMMERAGFCE-ZIFJQKEFSA-N |
| StdInChIKey = BRCPMMMERAGFCE-ZIFJQKEFSA-N |
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| SMILES = CC(C)CC(C(=O)N)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)CNC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C1CCCN1C(=O)C(Cc2ccc(cc2)O)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCSC)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCSC)NC(=O)C(Cc3ccccc3)NC(=O)CNC(=O)CNC(=O)C(Cc4ccc(cc4)O)N |
| SMILES = CC(C)CC(C(=O)N)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)CNC(=O)CNC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C1CCCN1C(=O)C(Cc2ccc(cc2)O)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCSC)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCSC)NC(=O)C(Cc3ccccc3)NC(=O)CNC(=O)CNC(=O)C(Cc4ccc(cc4)O)N |
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| InChI = InChI=1S/C131H200N30O43S2/c1-66(2)54-88(110(136)183)153-130(203)109(70(9)10)159-122(195)80(35-41-101(169)170)142-99(167)64-137-98(166)63-140-113(186)92(60-96(135)164)154-111(184)71(11)141-114(187)81(36-42-102(171)172)146-117(190)82(37-43-103(173)174)147-118(191)84(39-45-105(177)178)152-129(202)108(69(7)8)160-123(196)85(40-46-106(179)180)149-124(197)90(56-68(5)6)157-128(201)95-26-21-51-161(95)131(204)94(59-74-29-33-76(163)34-30-74)158-125(198)89(55-67(3)4)155-119(192)83(38-44-104(175)176)148-127(200)93(61-107(181)182)156-121(194)87(48-53-206-13)150-116(189)79(25-18-20-50-133)144-115(188)78(24-17-19-49-132)145-120(193)86(47-52-205-12)151-126(199)91(58-72-22-15-14-16-23-72)143-100(168)65-138-97(165)62-139-112(185)77(134)57-73-27-31-75(162)32-28-73/h14-16,22-23,27-34,66-71,77-95,108-109,162-163H,17-21,24-26,35-65,132-134H2,1-13H3,(H2,135,164)(H2,136,183)(H,137,166)(H,138,165)(H,139,185)(H,140,186)(H,141,187)(H,142,167)(H,143,168)(H,144,188)(H,145,193)(H,146,190)(H,147,191)(H,148,200)(H,149,197)(H,150,189)(H,151,199)(H,152,202)(H,153,203)(H,154,184)(H,155,192)(H,156,194)(H,157,201)(H,158,198)(H,159,195)(H,160,196)(H,169,170)(H,171,172)(H,173,174)(H,175,176)(H,177,178)(H,179,180)(H,181,182)/t71-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,108-,109-/m0/s1 |
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|Section2={{Chembox Properties |
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| Formula = C<sub>131</sub>H<sub>200</sub>N<sub>30</sub>O<sub>43</sub>S<sub>2</sub> |
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| MolarMass = 2947.29 g/mol |
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| Appearance = |
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| Density = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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'''Amidorphin''' is an [[endogenous]], [[C-terminus|C-terminally]] [[amide|amidated]], [[opioid]] [[peptide]] generated as a [[ |
'''Amidorphin''' is an [[endogenous]], [[C-terminus|C-terminally]] [[amide|amidated]], [[opioid]] [[peptide]] generated as a [[cleavage product]] of [[proenkephalin A]] in some mammalian species; in humans and most other species, the peptide is 1 residue longer and is not amidated. Amidorphin is widely distributed in the [[mammalian]] [[brain]], with particularly high concentrations found in the [[striatum]], and outside of the brain in [[adrenal medulla]] and [[posterior pituitary]].<ref name="pmid3965972">{{cite journal | author = Seizinger BR | title = Isolation and structure of a novel C-terminally amidated opioid peptide, amidorphin, from bovine adrenal medulla | journal = Nature | volume = 313 | issue = 5997 | pages = 57–9 | year = 1985 | pmid = 3965972 | doi =10.1038/313057a0 | author2 = Liebisch DC | author3 = Gramsch C | display-authors = 3 | last4 = Herz | first4 = A | last5 = Weber | first5 = E | last6 = Evans | first6 = CJ | last7 = Esch | first7 = FS | last8 = Böhlen | first8 = P | bibcode = 1985Natur.313...57S | s2cid = 4363051 }}</ref><ref name="pmid4045460">{{cite journal |vauthors=Liebisch DC, Seizinger BR, Michael G, Herz A | title = Novel opioid peptide amidorphin: characterization and distribution of amidorphin-like immunoreactivity in bovine, ovine, and porcine brain, pituitary, and adrenal medulla | journal = Journal of Neurochemistry | volume = 45 | issue = 5 | pages = 1495–503 |date=November 1985 | pmid = 4045460 | doi = 10.1111/j.1471-4159.1985.tb07218.x| s2cid = 12237293 }}</ref> The 26-residue peptide named amidorphin is found in several species including bovine (Bos taurus), sheep (Ovis aries), and pig (Sus scrofa). Humans and commonly studied lab animals (mice, rats) produce a 27-residue peptide that does not have an amidated C-terminal residue; this is due to the absence of a Gly in the precursor sequence and replacement with Ala, which is not a substrate for the amidating enzyme (Peptidyl-glycine alpha-amidating monooxygenase). The properties of the 27-residue peptide are presumably similar to those of amidorphin, although this has not been adequately tested. |
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In some brain areas, amidorphin is extensively further reduced into smaller fragments, such as the non-opioid peptide [[amidorphin-(8-26)]], or in humans, amidorphin-8-27. Cleavage of amidorphin into these smaller fragments releases the [[N-terminus|''N''-terminal]] [[Met-enkephalin|[Met]-enkephalin]] [[peptide sequence|sequence]] of amidorphin.<ref name="pmid3456613">{{cite journal |vauthors=Liebisch DC, Weber E, Kosicka B, Gramsch C, Herz A, Seizinger BR | title = Isolation and structure of a C-terminally amidated nonopioid peptide, amidorphin-(8-26), from bovine striatum: a major product of proenkephalin in brain but not in adrenal medulla | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 83 | issue = 6 | pages = 1936–40 |date=March 1986 | pmid = 3456613 | pmc = 323199 | doi = 10.1073/pnas.83.6.1936| bibcode = 1986PNAS...83.1936L | doi-access = free }}</ref> |
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* [[Opioid peptide]] |
* [[Opioid peptide]] |
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== |
==References== |
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{{Reflist}} |
{{Reflist|2}} |
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{{Analgesics}} |
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{{Opioid peptides}} |
{{Opioid peptides}} |
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{{ |
{{Opioidergics}} |
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[[Category:Analgesics]] |
[[Category:Analgesics]] |
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[[Category:Neurotransmitters]] |
[[Category:Neurotransmitters]] |
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[[Category: |
[[Category:Opioid peptides]] |
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[[sr:Amidorfin]] |