Amanin: Difference between revisions

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{{About|the toxin|the fictional beings with the same name|List of Star Wars races (A-E)#Amanin}}
{{About|the toxin|the fictional beings with the same name|Amanin (Star Wars)}}
{{Chembox
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 399502986
| verifiedrevid = 443949523
| ImageFile = Amanin.png
| ImageFile = Amanin.png
| ImageSize = 200px
| ImageSize = 200px
| IUPACName =
| IUPACName =
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 28316
| ChemSpiderID = 28316
| InChI = 1/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)
| InChI = 1/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)
| InChIKey = OFILNAORONITPV-UHFFFAOYAZ
| InChIKey = OFILNAORONITPV-UHFFFAOYAZ
| SMILES1 = O=C2N1CC(O)CC1C(=O)NC(C(=O)NC5C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CC(=O)O)CS(=O)c4c(c3ccc(O)cc3n4)C5)C(C)CC)C(C)C(O)C
| SMILES = CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H]2CS(=O)C3=C(C[C@@H](C(=O)NCC(=O)N1)NC(=O)[C@@H](NC(=O)[C@@H]4C[C@H](CN4C(=O)[C@@H](NC2=O)CC(=O)O)O)[C@@H](C)[C@H](CO)O)C5=CC=CC=C5N3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)
| StdInChI = 1S/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OFILNAORONITPV-UHFFFAOYSA-N
| StdInChIKey = OFILNAORONITPV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 21150-21-0
| CASNo = 21150-21-0
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem =
| UNII = VIW95I76GY
| SMILES = O=C(NCC(N[C@@](C(NCC(N[C@@H](C3)C(N[C@@H](CC(O)=O)C(N5[C@H]4C[C@@H](O)C5)=O)=O)=O)=O)([H])[C@@H](C)CC)=O)[C@H](CC1=C(S3=O)NC2=C1C=CC=C2)NC([C@@]([C@@H](C)[C@@H](O)CO)([H])N[C@@]4=O)=O
⚫
| PubChem = 30508
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Appearance =
| Appearance = | C=39 | H=53 | N=9 | O=14 | S=1
| C=39 | H=53 | N=9 | O=14 | S=1
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}


'''Amanin''' is a [[Cyclic compound|cyclic]] [[peptide]]. It is one of the [[amatoxin]]s, all of which are found in several members of the ''[[Amanita]]'' genus of [[mushroom]]s.
'''Amanin''' is a [[Cyclic compound|cyclic]] [[peptide]]. It is one of the [[amatoxin]]s, all of which are found in several members of the [[mushroom]] genus ''[[Amanita]]''.


==Toxicology==
==Toxicology==


Like other amatoxins, amanin is an inhibitor of [[RNA polymerase II]]. Upon ingestion, it binds to the RNA polymerase II enzyme which completely prevents [[Messenger RNA|mRNA synthesis]], effectively causing [[cytolysis]] of [[hepatocyte]]s (liver cells) and [[kidney|kidney cells]].<ref>{{cite journal | author = M. Cochet-Meillhac and Chambon P. | journal = Biochim Biophys Acta | volume = 353 | pages = 160–184 | year = 1974 | url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~ZI8h7t:1 | pmid = 4601749 | title = Animal DNA-dependent RNA polymerases. 11. Mechanism of the inhibition of RNA polymerases B by amatoxins | issue = 2}}</ref>
Like other amatoxins, amanin is an inhibitor of [[RNA polymerase II]]. Upon ingestion, it binds to the RNA polymerase II enzyme which completely prevents [[Messenger RNA|mRNA synthesis]], effectively causing [[cytolysis]] of [[hepatocyte]]s (liver cells) and [[kidney|kidney cells]].<ref>{{cite journal |author1 = M. Cochet-Meillhac |author2 =Chambon P. | journal = Biochim Biophys Acta | volume = 353 | pages = 160–184 | year = 1974 | url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~ZI8h7t:1 | doi = 10.1016/0005-2787(74)90182-8|pmid = 4601749 | title = Animal DNA-dependent RNA polymerases. 11. Mechanism of the inhibition of RNA polymerases B by amatoxins | issue = 2}}</ref>

⚫
==See also==
⚫
*[[Mushroom poisoning]]


==References==
==References==
{{Reflist}}
{{Reflist}}

⚫
==See also==
⚫
*[[Mushroom poisoning]]


{{Poisonous Amanitas}}
{{Poisonous Amanitas}}
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[[Category:Peptides]]
[[Category:Peptides]]
[[Category:Amatoxins]]
[[Category:Amatoxins]]
[[Category:Hepatology]]
[[Category:Hepatotoxins]]
[[Category:Transferase inhibitors]]
[[Category:Tryptamines]]
[[Category:Indoles]]

[[ca:Amanina]]
[[ja:アマニン]]

Latest revision as of 23:20, 24 June 2020

This article is about the toxin. For the fictional beings with the same name, see Amanin (Star Wars).
Amanin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55) checkY
    Key: OFILNAORONITPV-UHFFFAOYSA-N checkY
  • InChI=1/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)
    Key: OFILNAORONITPV-UHFFFAOYAZ
  • CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H]2CS(=O)C3=C(C[C@@H](C(=O)NCC(=O)N1)NC(=O)[C@@H](NC(=O)[C@@H]4C[C@H](CN4C(=O)[C@@H](NC2=O)CC(=O)O)O)[C@@H](C)[C@H](CO)O)C5=CC=CC=C5N3
Properties
C39H53N9O14S
Molar mass 903.96 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Amanin is a cyclic peptide. It is one of the amatoxins, all of which are found in several members of the mushroom genus Amanita.

Toxicology[edit]

Like other amatoxins, amanin is an inhibitor of RNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme which completely prevents mRNA synthesis, effectively causing cytolysis of hepatocytes (liver cells) and kidney cells.[1]

See also[edit]

References[edit]

  1. ^ M. Cochet-Meillhac; Chambon P. (1974). "Animal DNA-dependent RNA polymerases. 11. Mechanism of the inhibition of RNA polymerases B by amatoxins". Biochim Biophys Acta. 353 (2): 160–184. doi:10.1016/0005-2787(74)90182-8. PMID 4601749.
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