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T3D3589 - Amanullinic acid

Record Information
Version 1.0
Creation Date 2009-08-12 21:34:06 UTC
Update Date 2013-04-25 08:48:07 UTC
Accession Number T3D3589
Identification
Common Name Amanullinic acid
Description Amanullinic acid is one of a group of at least eight Amatoxins found in several genera of poisonous mushrooms, most notably Amanita phalloides and several other members of the genus Amanita, as well as some Conocybe, Galerina and Lepiota mushroom species. (W080)
Compound Type
  • Organic Compound
  • Mycotoxin
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms Not Available
Chemical Formula C39H53N9O13S
Average Molecular Weight 887.956
Monoisotopic Molecular Weight 887.348353517
Chemical IUPAC Name
[8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-13,34-bis(sec-butyl)-27$l^{4}-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.0^{6,10}.0^{18,26}.0^{19,24}]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetic acid
CAS Registry Number 54532-45-5
SMILES
CCC(C)C1NC(=O)CNC(=O)C2CC3=C(NC4=CC(O)=CC=C34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(O)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)CC)C(=O)N2
InChI Identifier
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)
InChI Key InChIKey=HFENEIQMWRYNGK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class Cyclic Peptides
Direct Parent Cyclic Peptides
Alternative Parents
  • Indoles
  • Phenols and Derivatives
  • 1,3-Aminoalcohols
  • Lactams
  • Tertiary Carboxylic Acid Amides
  • Pyrrolidines
  • Pyrroles
  • Polyols
  • Secondary Alcohols
  • Secondary Carboxylic Acid Amides
  • Sulfoxides
  • Enolates
  • Carboxylic Acids
  • Thioethers
Molecular Framework Aromatic Heteropolycyclic Compounds
Substituents
  • benzene
  • organonitrogen compound
  • thioether
  • organosulfur compound
  • enolate
  • phenol derivative
  • lactam
  • secondary alcohol
  • secondary carboxylic acid amide
  • carboxamide group
  • polyol
  • alkanolamine
  • alcohol
  • carboxylic acid
  • pyrrole
  • indole
  • pyrrolidine
  • tertiary carboxylic acid amide
  • sulfoxide
  • indole or derivative
  • 1,3-aminoalcohol
External Descriptors Not Available
DrugBank ID Not Available
PubChem Compound ID Not Available
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
CTD ID Not Available
Stitch ID Amanullinic acid Link_out
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Amanullinic_acid Link_out
Physical Properties
Appearance Not Available
Melting Point Not Available
Solubility Not Available
Predicted LogP -4.3843116303333325
Toxicity Profile
Route of Exposure Oral, dermal, inhalation, and parenteral (contaminated drugs). (W967)
Mechanism of Action The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
Metabolism Not Available
Toxicity Values LD50: >20 mg/kg (Mouse) (W530)
Lethal Dose 0.1 mg/kg for an adult human. (W080)
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Amatoxins are a subgroup of at least eight toxic compounds found in several genera of poisonous mushrooms, most notably Amanita phalloides and several other members of the genus Amanita, as well as some Conocybe, Galerina and Lepiota mushroom species. (W080)
Minimum Risk Level Not Available
Health Effects Amatoxins cause liver damage. They may also affect the kidneys. The most severe effects are toxic hepatitis with centrolobular necrosis and hepatic steatosis, as well as acute tubulointerstitial nephropathy, which altogether induce a severe hepatorenal syndrome. (W080)
Symptoms Diarrhea and cramps are the first symptoms. (W081)
Treatment Treatment involves high dose penicillin as well as supportive care in cases of hepatic and renal injury. Cautious attention is given to maintaining hemodynamic stability, although if hepatorenal syndrome has developed the prognosis is guarded at best. (W080)
References
General References
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]
  • W081 — Wikipedia. alpha-Amanitin. Last Updated 9 July 2009. [Link]
  • W455 — Wikipedia. Mushroom poisoning. Last Updated 10 August 2009. [Link]
  • W967 — Peraica M, Domijan AM. Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 Link_out]

Targets

1. DNA-directed RNA polymerase II subunit RPB1

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Largest and catalytic component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Forms the polymerase active center together with the second largest subunit. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB1 is part of the core element with the central large cleft, the clamp element that moves to open and close the cleft and the jaws that are thought to grab the incoming DNA template. At the start of transcription, a single stranded DNA template strand of the promoter is positioned within the central active site cleft of Pol II. A bridging helix emanates from RPB1 and crosses the cleft near the catalytic site and is thought to promote translocation of Pol II by acting as a ratchet that moves the RNA-DNA hybrid through the active site by switching from straight to bent conformations at each step of nucleotide addition. During transcription elongation, Pol II moves on the template as the transcript elongates. Elongation is influenced by the phosphorylation status of the C-terminal domain (CTD) of Pol II largest subunit (RPB1), which serves as a platform for assembly of factors that regulate transcription initiation, elongation, termination and mRNA processing. Acts as a RNA-dependent RNA polymerase when associated with small delta antigen of Hepatitis delta virus, acting both as a replicate and transcriptase for the viral RNA circular genome.

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P24928 Link_out
Gene: POLR2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

2. DNA-directed RNA polymerase II subunit RPB11-a

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB11 is part of the core element with the central large cleft (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P52435 Link_out
Gene: POLR2J Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

3. DNA-directed RNA polymerase II subunit RPB11-b1

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB11 is part of the core element with the central large cleft (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: Q9GZM3 Link_out
Gene: POLR2J2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

4. DNA-directed RNA polymerase II subunit RPB11-b2

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB11 is part of the core element with the central large cleft (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: Q9H1A7 Link_out
Gene: POLR2J3 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

5. DNA-directed RNA polymerase II subunit RPB2

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Second largest component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Proposed to contribute to the polymerase catalytic activity and forms the polymerase active center together with the largest subunit. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB2 is part of the core element with the central large cleft, the clamp element that moves to open and close the cleft and the jaws that are thought to grab the incoming DNA template (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P30876 Link_out
Gene: POLR2B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

6. DNA-directed RNA polymerase II subunit RPB3

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB3 is part of the core element with the central large cleft and the clamp element that moves to open and close the cleft (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P19387 Link_out
Gene: POLR2C Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

7. DNA-directed RNA polymerase II subunit RPB4

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB4 is part of a subcomplex with RPB7 that binds to a pocket formed by RPB1, RPB2 and RPB6 at the base of the clamp element. The RBP4-RPB7 subcomplex seems to lock the clamp via RPB7 in the closed conformation thus preventing double stranded DNA to enter the active site cleft. The RPB4-RPB7 subcomplex binds single-stranded DNA and RNA (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: O15514 Link_out
Gene: POLR2D Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

8. DNA-directed RNA polymerase II subunit RPB7

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB7 is part of a subcomplex with RPB4 that binds to a pocket formed by RPB1, RPB2 and RPB6 at the base of the clamp element. The RBP4-RPB7 subcomplex seems to lock the clamp via RPB7 in the closed conformation thus preventing double stranded DNA to enter the active site cleft. The RPB4-RPB7 subcomplex binds single-stranded DNA and RNA (By similarity). Binds RNA.

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P62487 Link_out
Gene: POLR2G Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

9. DNA-directed RNA polymerase II subunit RPB9

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Component of RNA polymerase II which synthesizes mRNA precursors and many functional non-coding RNAs. Pol II is the central component of the basal RNA polymerase II transcription machinery. It is composed of mobile elements that move relative to each other. RPB9 is part of the upper jaw surrounding the central large cleft and thought to grab the incoming DNA template (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P36954 Link_out
Gene: POLR2I Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

10. DNA-directed RNA polymerases I, II, and III subunit RPABC1

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Common component of RNA polymerases I, II and III which synthesize ribosomal RNA precursors, mRNA precursors and many functional non-coding RNAs, and small RNAs, such as 5S rRNA and tRNAs, respectively. Pol II is the central component of the basal RNA polymerase II transcription machinery. Pols are composed of mobile elements that move relative to each other. In Pol II, POLR2E/RPB5 is part of the lower jaw surrounding the central large cleft and thought to grab the incoming DNA template. Seems to be the major component in this process (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P19388 Link_out
Gene: POLR2E Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

11. DNA-directed RNA polymerases I, II, and III subunit RPABC2

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Common component of RNA polymerases I, II, and III which synthesize ribosomal RNA precursors, mRNA precursors and many functional non-coding RNAs, and small RNAs, such as 5S rRNA and tRNAs, respectively. Pol II is the central component of the basal RNA polymerase II transcription machinery. Pols are composed of mobile elements that move relative to each other. In Pol II, POLR2F/RPB6 is part of the clamp element and togther with parts of RPB1 and RPB2 forms a pocket to which the RPB4-RPB7 subcomplex binds (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P61218 Link_out
Gene: POLR2F Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

12. DNA-directed RNA polymerases I, II, and III subunit RPABC3

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Common component of RNA polymerases I, II and III which synthesize ribosomal RNA precursors, mRNA precursors and many functional non-coding RNAs, and small RNAs, such as 5S rRNA and tRNAs, respectively.

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P52434 Link_out
Gene: POLR2H Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

13. DNA-directed RNA polymerases I, II, and III subunit RPABC4

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Common component of RNA polymerases I, II and III which synthesize ribosomal RNA precursors, mRNA precursors and many functional non-coding RNAs, and a small RNAs, such as 5S rRNA and tRNAs, respectively.

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P53803 Link_out
Gene: POLR2K Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]

14. DNA-directed RNA polymerases I, II, and III subunit RPABC5

DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. Common component of RNA polymerases I, II and III which synthesize ribosomal RNA precursors, mRNA precursors and many functional non-coding RNAs, and a small RNAs, such as 5S rRNA and tRNAs, respectively. Pol II is the central component of the basal RNA polymerase II transcription machinery. Pols are composed of mobile elements that move relative to each other. In Pol II, POLR2L/RBP10 is part of the core element with the central large cleft (By similarity).

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (W080)
UniProt ID: P62875 Link_out
Gene: POLR2L Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W080 — Wikipedia. Amatoxin. Last Updated 31 July 2009. [Link]