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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChemSpiderID InChI InChIKey SMILES1 InChI1->InChI.
Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.
Line 11: Line 11:
| InChIKey = BOHCOUQZNDPURZ-UHFFFAOYAZ
| InChIKey = BOHCOUQZNDPURZ-UHFFFAOYAZ
| SMILES1 = O=C2N1CC(O)CC1C(=O)NC(C(=O)NC5C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CC(=O)N)CS(=O)c4c(c3ccccc3n4)C5)C(C)CC)C(C)C(O)CO
| SMILES1 = O=C2N1CC(O)CC1C(=O)NC(C(=O)NC5C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CC(=O)N)CS(=O)c4c(c3ccccc3n4)C5)C(C)CC)C(C)C(O)CO
| StdInChI = 1S/C39H54N10O13S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-63(62)38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)
| StdInChIKey = BOHCOUQZNDPURZ-UHFFFAOYSA-N
| CASNo=58311-65-2
| CASNo=58311-65-2
| PubChem=3035225
| PubChem=3035225

Revision as of 11:46, 29 November 2010

Amaninamide
File:Amaninamide 3d.png
Names
Other names
4-(2-mercapto-L-tryptophan)-alpha-Amanitin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C39H54N10O13S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-63(62)38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)
    Key: BOHCOUQZNDPURZ-UHFFFAOYSA-N
  • InChI=1/C39H54N10O13S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-63(62)38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)
    Key: BOHCOUQZNDPURZ-UHFFFAOYAZ
  • O=C(NCC(N[C@@](C(NCC(N[C@@H](C3)C(N[C@@H](CC(N)=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
  • O=C2N1CC(O)CC1C(=O)NC(C(=O)NC5C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)NC2CC(=O)N)CS(=O)c4c(c3ccccc3n4)C5)C(C)CC)C(C)C(O)CO
Properties
C39H54N10O13S
Molar mass 902.97 g/mol
Appearance Colorless, crystalline solid
Soluble
Solubility in ethanol, methanol Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Toxicology

Like other amatoxins, amaninamide 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]

References

  1. ^ M. Cochet-Meillhac and 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. PMID 4601749.

See also

External links

source: https://en.wikipedia.org/w/index.php?diff=399503108&oldid=395535224

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