T3DB: Ibotenic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (12)XML

Targets (12)

Record Information

Version

2.0

Creation Date

2009-07-03 20:59:52 UTC

Update Date

2014-12-24 20:25:31 UTC

Accession Number

T3D2455

Identification

Common Name

Ibotenic acid

Class

Small Molecule

Description

Ibotenic acid is a chemical compound that is naturally occurring in the mushrooms Amanita muscaria and Amanita pantherina, among others. Ibotenic acid is a powerful neurotoxin that is used as a brain-lesioning agent and has shown to be highly neurotoxic when injected directly into the brains of mice and rats. In 1960's, ibotenic acid was originally isolated from Amanita ibotengutake in Japan. A. ibotengutake is very like to A. pantherina. (2)

Compound Type

Amine
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
(alpha)-Ibotenic acid
4-Isoxazoline-5-acetic acid, alpha-amino-3-oxo- (8ci)
alpha-amino-2,3-dihydro-3-oxo-5-Isoxazoleacetic acid
alpha-amino-3-Hydroxy-5-isoxazoleacetic acid
Amanita muscaria
Ibotenate

Chemical Formula

C₅H₆N₂O₄

Average Molecular Mass

158.112 g/mol

Monoisotopic Mass

158.033 g/mol

CAS Registry Number

2552-55-8

IUPAC Name

(2S)-2-amino-2-(3-hydroxy-1,2-oxazol-5-yl)acetic acid

Traditional Name

(S)-amino(3-hydroxy-1,2-oxazol-5-yl)acetic acid

SMILES

N[C@H](C(O)=O)C1=CC(O)=NO1

InChI Identifier

InChI=1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)/t4-/m0/s1

InChI Key

InChIKey=IRJCBFDCFXCWGO-BYPYZUCNSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Aralkylamine
Azole
Isoxazole
Heteroaromatic compound
Lactam
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Amine
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	43.8 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.9	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	1	ChemAxon
pKa (Strongest Basic)	6.94	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	33.98 m³·mol⁻¹	ChemAxon
Polarizability	13.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bt9-3900000000-538b3dc6e414dc488aa9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3900000000-e2e4c32d8a8314544cba	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0059-9000000000-e385f0e12d73b3cd3cb7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-b6c180dc6911b7905330	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06si-9700000000-5c57783e7267d6413ac1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-435009ab753438d92ac4	2016-08-03	View Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (1)

Mechanism of Toxicity

A portion of ibotenic acid is metabolized to muscimol, a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets. (3, 4)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Ibotenic acid is used as a brain lesioning agent in the medical environment. When injected intracranially, ibotenic acid causes the development of lesions of the brain. (2)

Minimum Risk Level

Not Available

Health Effects

Ibotenic acid is neurotoxic. (2)

Symptoms

When ibotenic acid is ingested, a small portion is decarboxylated into muscimol. Ibotenic acid evokes entheogenic effects in human beings at doses in range of 50-100 mg. Peak intoxication is reached approximately 2-3 hours after oral ingestion, consisting of one or all of the following; visual distortions/hallucinations, loss of equilibrium, muscle twitching (commonly mislabeled as convulsions), and altered sensory perception. These effects generally last for 6-8 hours, varying with dose. (2)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

1233

ChEMBL ID

Not Available

ChemSpider ID

Not Available

KEGG ID

C10600

UniProt ID

Not Available

OMIM ID

ChEBI ID

25520

BioCyc ID

Not Available

CTD ID

D007051

Stitch ID

Ibotenic acid

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Ibotenic_acid

References

Synthesis Reference

Not Available

MSDS

T3D2455.pdf

General References

Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Wikipedia. Ibotenic acid. Last Updated 17 June 2009. [Link]
Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Gamma-aminobutyric acid receptor subunit alpha-1

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular Weight:: 51801.395 Da

References

Target Details

2. Gamma-aminobutyric acid receptor subunit alpha-2

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA2
Uniprot ID:: P47869
Molecular Weight:: 51325.85 Da

References

Target Details

3. Gamma-aminobutyric acid receptor subunit alpha-3

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA3
Uniprot ID:: P34903
Molecular Weight:: 55164.055 Da

References

Target Details

4. Gamma-aminobutyric acid receptor subunit alpha-4

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA4
Uniprot ID:: P48169
Molecular Weight:: 61622.645 Da

References

Target Details

5. Gamma-aminobutyric acid receptor subunit alpha-5

General Function:: Transporter activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA5
Uniprot ID:: P31644
Molecular Weight:: 52145.645 Da

References

Target Details

6. Gamma-aminobutyric acid receptor subunit alpha-6

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA6
Uniprot ID:: Q16445
Molecular Weight:: 51023.69 Da

References

Target Details

7. Gamma-aminobutyric acid receptor subunit gamma-1

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRG1
Uniprot ID:: Q8N1C3
Molecular Weight:: 53594.49 Da

References

Target Details

8. Gamma-aminobutyric acid receptor subunit gamma-2

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:: GABRG2
Uniprot ID:: P18507
Molecular Weight:: 54161.78 Da

References

Target Details

9. Gamma-aminobutyric acid receptor subunit gamma-3

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRG3
Uniprot ID:: Q99928
Molecular Weight:: 54288.16 Da

References

Target Details

10. Metabotropic glutamate receptor 2

General Function:: Group ii metabotropic glutamate receptor activity
Specific Function:: G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. May mediate suppression of neurotransmission or may be involved in synaptogenesis or synaptic stabilization.
Gene Name:: GRM2
Uniprot ID:: Q14416
Molecular Weight:: 95566.715 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	>10 uM	Not Available	BindingDB 82355

References

Target Details

11. Metabotropic glutamate receptor 4

General Function:: Group iii metabotropic glutamate receptor activity
Specific Function:: G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Signaling inhibits adenylate cyclase activity.
Gene Name:: GRM4
Uniprot ID:: Q14833
Molecular Weight:: 101866.835 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	>10 uM	Not Available	BindingDB 82355

References

Target Details

12. Metabotropic glutamate receptor 6

General Function:: Protein homodimerization activity
Specific Function:: G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity (By similarity). Signaling stimulates TRPM1 channel activity and Ca(2+) uptake. Required for normal vision.
Gene Name:: GRM6
Uniprot ID:: O15303
Molecular Weight:: 95466.77 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	>10 uM	Not Available	BindingDB 82355

References

Ibotenic acid (T3D2455)

Structure for T3D2455: Ibotenic acid

Targets

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Binding/Activity Constants

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