:Amanullinic acid

{{chembox

| verifiedrevid = 443948153

| ImageFile=Amanullinic acid structure.png

| ImageSize=200px

| ImageFile1=Amanullinic acid with tube model.png

| ImageSize1=200px

| IUPACName=

| OtherNames=1-L-Aspartic acid-3-isoleucine-alpha-amanitin

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 149798

| InChI = 1/C39H53N9O13S/c1-5-17(3)31-36(58)41-13-28(51)42-26-16-62(61)38-22(21-8-7-19(49)9-23(21)45-38)11-24(33(55)40-14-29(52)46-31)43-37(59)32(18(4)6-2)47-35(57)27-10-20(50)15-48(27)39(60)25(12-30(53)54)44-34(26)56/h7-9,17-18,20,24-27,31-32,45,49-50H,5-6,10-16H2,1-4H3,(H,40,55)(H,41,58)(H,42,51)(H,43,59)(H,44,56)(H,46,52)(H,47,57)(H,53,54)

| InChIKey = HFENEIQMWRYNGK-UHFFFAOYAM

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C39H53N9O13S/c1-5-17(3)31-36(58)41-13-28(51)42-26-16-62(61)38-22(21-8-7-19(49)9-23(21)45-38)11-24(33(55)40-14-29(52)46-31)43-37(59)32(18(4)6-2)47-35(57)27-10-20(50)15-48(27)39(60)25(12-30(53)54)44-34(26)56/h7-9,17-18,20,24-27,31-32,45,49-50H,5-6,10-16H2,1-4H3,(H,40,55)(H,41,58)(H,42,51)(H,43,59)(H,44,56)(H,46,52)(H,47,57)(H,53,54)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HFENEIQMWRYNGK-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=54532-45-5

| PubChem=171349

| 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(O)=C2)NC([C@@]([C@@H](C)CC)([H])N[C@@]4=O)=O

}}

|Section2={{Chembox Properties

| Formula=C39H53N9O13S

| MolarMass=887.96 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

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|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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Amanullinic acid is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in several members of the mushroom genus Amanita. Amanullinic acid is relatively non-toxic( oral {{LD50}} >20 mg/kg in mice).{{cite journal |author1 = T. Wieland |author2 =Faulstich H. | journal = CRC Critical Reviews in Biochemistry | volume = 5 | pages = 185–260 | year = 1978 | doi = 10.3109/10409237809149870 | title = Amatoxins, Phallotoxins, Phallolysin, and Antamanide: the Biologically Active Components of Poisonous Amanita Mushrooms | pmid = 363352 | issue = 3}}

Toxicology

Like other amatoxins, amanullinic acid is an inhibitor of RNA polymerase II.

See also

References

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