Amanullinic acid

Amanullinic acid
Names


Other names 1-L-Aspartic acid-3-isoleucine-alpha-amanitin
Identifiers
CAS Registry Number	54532-45-5^Y
ChemSpider	149798^Y
InChI InChI=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)^Y Key: HFENEIQMWRYNGK-UHFFFAOYSA-N^Y 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) Key: HFENEIQMWRYNGK-UHFFFAOYAM
Jmol-3D images	Image Image
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 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)CC
Properties
Chemical formula	C₃₉H₅₃N₉O₁₃S
Molar mass	887.96 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Amanullinic acid is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in several members of the Amanita genus of mushrooms. The oral LD₅₀ of amanullinic acid is approximately 0.1 mg/kg in mice.^[1]

Toxicology

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

↑ T. Wieland and Faulstich H. (1978). "Amatoxins, Phallotoxins, Phallolysin, and Antamanide: the Biologically Active Components of Poisonous Amanita Mushrooms". CRC Critical Reviews in Biochemistry 5 (3): 185–260. doi:10.3109/10409237809149870. PMID 363352.

Poisoning from Amanitas

sect.
Amanita

Species	A. albocreata A. crenulata A. farinosa A. frostiana A. gemmata A. multisquamosa A. muscaria A. pantherina A. porphyria A. regalis A. strobiliformis A. xanthocephala

Compounds	Toxins: Ibotenic Acid Muscimol Other compounds: Muscarine Muscazone Amavadine

sect.
Phalloidea

Species

Destroying angels	A. bisporigera A. exitialis A. magnivelaris A. ocreata A. verna A. virosa A. virosiformis

Other members	A. arocheae A. phalloides A. subjunquilea

Compounds

Amatoxins	Amanitins alpha- beta- gamma- epsilon- Amanullin Amanullinic acid Amaninamide Amanin Proamanullin

Phallotoxins	Phallacidin Phallacin Phallisacin Phallisin Phalloidin Phalloin Prophalloin

Other compounds	Antamanide Phallolysin Toxophallin

sect.
Lepidella

Species	A. nauseosa A. proxima A. smithiana A. sphaerobulbosa A. thiersii

Compounds	Allenic norleucine (2-amino-4,5-hexadienoic acid) Propargylglycine

sect.
Validae

Species	A. rubescens (A. amerirubescens nom. prov.)

Compounds	Rubescenslysin

Clostridium:	tetani Tetanospasmin Tetanolysin perfringens Alpha toxin Enterotoxin difficile A B botulinum Botox

other:	Anthrax toxin Listeriolysin O

Streptolysin Leukocidin Panton-Valentine leukocidin

Staphylococcus	Staphylococcus aureus alpha/beta/delta Exfoliatin Toxic shock syndrome toxin Staphylococcal Enterotoxin B (SEB)

Endotoxin

Plant toxins

scorpion:	Androctonus australis hector insect toxin Charybdotoxin Maurotoxin Agitoxin Margatoxin Slotoxin Scyllatoxin Hefutoxin Lq2 Birtoxin Bestoxin BmKAEP Phaiodotoxin Imperatoxin Pi3

spider:	Latrotoxin Alpha-latrotoxin CSTX Cupiennins PhTx3 Stromatoxin Vanillotoxin Huwentoxin

mollusca:	Conotoxin Eledoisin Onchidal Saxitoxin Tetrodotoxin

fish:	Ciguatera Tetrodotoxin

amphibian:	(+)-Allopumiliotoxin 267A Batrachotoxin Bufotoxins Arenobufagin Bufotalin Bufotenin Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin

reptile/snake venom:	Bungarotoxin Alpha-Bungarotoxin Beta-Bungarotoxin Calciseptine Taicatoxin Calcicludine Cardiotoxin III

note: some toxins are produced by lower species and pass through intermediate species