Amanullinic acid: Difference between revisions

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	{{chembox		{{chembox
	\| verifiedrevid = ~~399503245~~		\| verifiedrevid = 443948153
	\|ImageFile=Amanullinic acid structure.png		\| ImageFile=Amanullinic acid structure.png
	\|ImageSize=200px		\| ImageSize=200px
	\|ImageFile1=Amanullinic acid with tube model.png		\| ImageFile1=Amanullinic acid with tube model.png
	\|ImageSize1=200px		\| ImageSize1=200px
	\|IUPACName=		\| IUPACName=
	\|OtherNames=1-L-Aspartic acid-3-isoleucine-alpha-amanitin		\| OtherNames=1-L-Aspartic acid-3-isoleucine-alpha-amanitin
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 149798		\| 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)		\| 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		\| InChIKey = HFENEIQMWRYNGK-UHFFFAOYAM
	\| 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)CC
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| 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)		\| 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_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = HFENEIQMWRYNGK-UHFFFAOYSA-N		\| StdInChIKey = HFENEIQMWRYNGK-UHFFFAOYSA-N
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo=54532-45-5		\| CASNo=54532-45-5
	\| PubChem=171349		\| PubChem=171349
	\| SMILES=O=C(NCC(N(C(NCC(N(C3)C(N(CC(O)=O)C(N54C(O)C5)=O)=O)=O)=O)()(C)CC)=O)(CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC(((C)CC)()N4=O)=O		\| SMILES = O=C(NCC(N(C(NCC(N(C3)C(N(CC(O)=O)C(N54C(O)C5)=O)=O)=O)=O)()(C)CC)=O)(CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC(((C)CC)()N4=O)=O
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula=C<sub>39</sub>H<sub>53</sub>N<sub>9</sub>O<sub>13</sub>S		\| Formula=C<sub>39</sub>H<sub>53</sub>N<sub>9</sub>O<sub>13</sub>S
	\| MolarMass=887.96 g/mol		\| MolarMass=887.96 g/mol
	\| Appearance=		\| Appearance=
	\| Density=		\| Density=
	\| MeltingPt=		\| MeltingPt=
	\| BoilingPt=		\| BoilingPt=
	\| Solubility=		\| Solubility=
	}}		}}
	\|Section3= {{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
			\| AutoignitionPt =
	\| Autoignition=
	}}		}}
	}}		}}

	'''Amanullinic acid''' is a ] ]. It is an ], all of which are found in several members of the '']'' genus of ]s. ~~The~~ oral {{LD50}} ~~of amanullinic acid is approximately 0.1~~ mg/kg in mice.<ref>{{cite journal \| ~~author~~ = T. Wieland ~~and~~ Faulstich H. \| journal = CRC Critical Reviews in Biochemistry \| volume = 5 \| pages = ~~185~~ \| year = 1978 \| doi = 10.3109/10409237809149870 \| title = Amatoxins, Phallotoxins, Phallolysin, and Antamanide: the Biologically Active Components of Poisonous Amanita Mushrooms \| pmid = 363352 \| issue = 3}}</ref>		'''Amanullinic acid''' is a ] ]. It is an ], all of which are found in several members of the ] genus '']''. Amanullinic acid is relatively non-toxic( oral {{LD50}} >20 mg/kg in mice).<ref>{{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}}</ref>

	==Toxicology==		==Toxicology==
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	==External links==		==External links==
	*		* {{Webarchive\|url=https://web.archive.org/web/20090113180522/http://dohs.ors.od.nih.gov/pdf/Amatoxins%20REVISED.pdf \|date=2009-01-13 }}

	{{Poisonous Amanitas}}		{{Poisonous Amanitas}}
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	]		]
	]		]
	]		]

	]

Latest revision as of 07:35, 16 March 2023

Amanullinic acid
Names


Other names 1-L-Aspartic acid-3-isoleucine-alpha-amanitin
Identifiers
CAS Number	54532-45-5
3D model (JSmol)	Interactive image
ChemSpider	149798
PubChem CID	171349
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)Key: HFENEIQMWRYNGK-UHFFFAOYSA-N 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
SMILES O=C(NCC(N(C(NCC(N(C3)C(N(CC(O)=O)C(N54C(O)C5)=O)=O)=O)=O)()(C)CC)=O)(CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC(((C)CC)()N4=O)=O
Properties
Chemical formula	C₃₉H₅₃N₉O₁₃S
Molar mass	887.96 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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).

Toxicology

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

References

T. Wieland; 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.

External links

Amatoxins REVISED Archived 2009-01-13 at the Wayback Machine

Poisonous Amanita mushrooms

Subgenus
Amanita

Amanita

Species	A. albocreata A. crenulata A. farinosa A. frostiana A. gemmata A. ibotengutake A. multisquamosa A. muscaria A. pantherina A. porphyria A. regalis A. strobiliformis A. xanthocephala
Compounds	Toxins: Ibotenic Acid Muscimol Other compounds: Muscarine Muscazone Amavadine

Subgenus
Amanitina

Lepidella
(=Saproamanita)

Species	A. thiersii
Compounds	unknown toxin

Phalloideae

Species

Destroying angels	A. bisporigera A. exitialis A. magnivelaris A. ocreata A. verna A. virosa A. virosiformis
Other members	A. arocheae A. fuliginea A. fuligineoides A. pallidorosea A. phalloides A. rimosa A. subjunquillea

Compounds

Amatoxins	Amanitins alpha- beta- gamma- epsilon- Amanullin Amanullinic acid Amaninamide Amanin Proamanullin
Phallotoxins	Phallacidin Phallacin Phallisacin Phallisin Phalloidin Phalloin Prophalloin
Virotoxins	Alaviroidin Viroisin Deoxoviroisin Viroidin Deoxoviroidin
Other compounds	Antamanide Phallolysin Toxophallin

Roanokenses

Species	A. proxima A. smithiana A. sphaerobulbosa
Compounds	Allenic norleucine (2-amino-4,5-hexadienoic acid) Propargylglycine

Validae

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

Toxins

Clostridium:	tetani Tetanospasmin Tetanolysin perfringens Alpha toxin Enterotoxin difficile A B botulinum Botox
Other:	Anthrax toxin Listeriolysin O

Cocci

Streptolysin Leukocidin Panton–Valentine leukocidin
Staphylococcus	Staphylococcus aureus alpha/beta/delta Exfoliatin Toxic shock syndrome toxin Staphylococcal Enterotoxin B (SEB)

Lipopolysaccharide
- Lipid A
Bacillus thuringiensis delta endotoxin
- Cry1Ac
- Cry3Bb1
Other B. thuringiensis toxins
- Cry6Aa
- Cry34Ab1

Virulence
factor

Mycotoxins

Aflatoxin
Amatoxin (alpha-amanitin, beta-amanitin, gamma-amanitin, epsilon-amanitin)
beta-Nitropropionic acid
Citrinin
Cytochalasin
Ergotamine
Fumonisin (Fumonisin B1, Fumonisin B2, Fumonisin B3, Fumonisin B4)
Gliotoxin
Ibotenic acid
Lolitrem B
Muscimol
Orellanine
Ochratoxin
Patulin
Phalloidin
Sterigmatocystin
Trichothecene
Vomitoxin
Zeranol
Zearalenone

Plant toxins

Invertebrate
toxins

Scorpion:	Androctonus australis hector insect toxin Charybdotoxin Maurotoxin Agitoxin Margatoxin Slotoxin Scyllatoxin Hefutoxin HgeTx1 HsTx1 Kaliotoxin Lq2 Birtoxin Bestoxin BmKAEP Phaiodotoxin Imperatoxin Pi3
Spider:	Latrotoxin Alpha-latrotoxin CSTX Cupiennins PhTx3 Stromatoxin Vanillotoxin Huwentoxin
Mollusca:	Conotoxin Eledoisin Onchidal Saxitoxin Tetrodotoxin

Vertebrate
toxins

Fish:	Ciguatoxin Tetrodotoxin
Amphibian:	(+)-Allopumiliotoxin 267A Batrachotoxin Bufotoxins Arenobufagin Bufotalin Bufotenin Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB
Reptile/ Snake venom:	Bungarotoxin α-Bungarotoxin β-Bungarotoxin Calciseptine Taicatoxin Calcicludine Cardiotoxin III

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

Category

Categories:

Misplaced Pages

Amanullinic acid: Difference between revisions

Latest revision as of 07:35, 16 March 2023

Toxicology

See also

References

External links