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Record Information
Version2.0
Creation Date2009-07-03 20:59:52 UTC
Update Date2014-12-24 20:25:31 UTC
Accession NumberT3D2455
Identification
Common NameIbotenic acid
ClassSmall Molecule
DescriptionIbotenic 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
Thumb
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 FormulaC5H6N2O4
Average Molecular Mass158.112 g/mol
Monoisotopic Mass158.033 g/mol
CAS Registry Number2552-55-8
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
SMILESN[C@H](C(O)=O)C1=CC(O)=NO1
InChI IdentifierInChI=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 KeyInChIKey=IRJCBFDCFXCWGO-BYPYZUCNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility43.8 mg/mLALOGPS
logP-2.4ALOGPS
logP-2.9ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)1ChemAxon
pKa (Strongest Basic)6.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.58 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.98 m3·mol-1ChemAxon
Polarizability13.42 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-3900000000-538b3dc6e414dc488aa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-e2e4c32d8a8314544cbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-9000000000-e385f0e12d73b3cd3cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-b6c180dc6911b7905330View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06si-9700000000-5c57783e7267d6413ac1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-435009ab753438d92ac4View in MoNA
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (1)
Mechanism of ToxicityA 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)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIbotenic 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 LevelNot Available
Health EffectsIbotenic acid is neurotoxic. (2)
SymptomsWhen 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)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID1233
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC10600
UniProt IDNot Available
OMIM ID
ChEBI ID25520
BioCyc IDNot Available
CTD IDD007051
Stitch IDIbotenic acid
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkIbotenic_acid
References
Synthesis ReferenceNot Available
MSDST3D2455.pdf
General References
  1. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  2. Wikipedia. Ibotenic acid. Last Updated 17 June 2009. [Link]
  3. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  4. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
  1. Wikipedia. Muscimol. Last Updated 5 June 2009. [Link]
  2. eMedicine (2008). Toxicity, Mushrooms - Ibotenic Acid. [Link]
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
TypeValueAssay TypeAssay Source
Inhibitory>10 uMNot AvailableBindingDB 82355
References
  1. Conn PJ, Pin JP: Pharmacology and functions of metabotropic glutamate receptors. Annu Rev Pharmacol Toxicol. 1997;37:205-37. [9131252 ]
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
TypeValueAssay TypeAssay Source
Inhibitory>10 uMNot AvailableBindingDB 82355
References
  1. Conn PJ, Pin JP: Pharmacology and functions of metabotropic glutamate receptors. Annu Rev Pharmacol Toxicol. 1997;37:205-37. [9131252 ]
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
TypeValueAssay TypeAssay Source
Inhibitory>10 uMNot AvailableBindingDB 82355
References
  1. Conn PJ, Pin JP: Pharmacology and functions of metabotropic glutamate receptors. Annu Rev Pharmacol Toxicol. 1997;37:205-37. [9131252 ]