Compound: Ibotenic acid
SMILES: O=c1[nH]oc(c1)C(N)C(=O)O
InChIKey: IRJCBFDCFXCWGO-UHFFFAOYSA-N
Synonyms: Ibotenic acid, 2552-55-8, DL-Ibotenic acid, (RS)-Ibotenic acid, 44AS82FRSI, alpha-Amino-2,3-dihydro-3-oxo-5-isoxazoleacetic acid, 2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid, DTXSID40893771, 5-Isoxazoleacetic acid, alpha-amino-2,3-dihydro-3-oxo-, NSC-204850, 2-amino-2-(3-oxoisoxazol-5-yl)acetic acid, 4-Isoxazoline-5-acetic acid, alpha-amino-3-oxo-, Acid, Ibotenic, 2-Azaniumyl-2-(3-oxo-1,2-oxazol-5-yl)acetate, (+-)-Ibotenic acid, RefChem:789640, DTXCID701323806, 637-415-7, Ibotenate, (+/-)-Ibotenic acid, 2-amino-2-(3-oxo-2,3-dihydroisoxazol-5-yl)acetic acid, MFCD00069294, alpha-Amino-3-hydroxy-5-isoxazoleacetic acid, NSC204850, CHEMBL284895, (RS)-Ibotenic acid;DL-Ibotenic acid, 2-amino-2-(3-hydroxyisoxazol-5-yl)acetic acid, 5-Isoxazoleacetic acid,a-amino-2,3-dihydro-3-oxo-, 5-Isoxazoleaceticacid,-alpha--amino-2,3-dihydro-3-oxo-,(-alpha-R)-(9CI), SR-01000075462, UNII-44AS82FRSI, NSC 204850, IRJCBFDCFXCWGO-UHFFFAOYSA-N, DL-Ibotenic acid;, (y)-Ibotenic acid, (?)-Ibotenic acid, IBOTENIC ACID [MI], Lopac0_000651, MLS002153141, SCHEMBL153359, 4-Isoxazoline-5-acetic acid, .alpha.-amino-3-oxo-, Ibotenic acid, ~95%, solid, CHEBI:5854, GTPL1371, orb1679003, orb3012980, SCHEMBL4582627, IBOTENIC ACID [WHO-DD], 5-Isoxazoleaceticacid,-alpha--amino-2,3-dihydro-3-oxo-,(-alpha-S)-(9CI), BDBM82355, 5-Isoxazoleacetic acid, .alpha.-amino-2,3-dihydro-3-oxo-, MSK7269, HMS2230A08, HMS3262C03, HMS3266E19, HMS3369N13, HMS3414F03, HMS3678F03, IBOTENIC ACID, (+/-)-, HY-N2311, NSC_1233, Tox21_500651, HB0330, PDSP1_001426, PDSP2_001410, AKOS006228673, AKOS027320609, CCG-204738, EBC-616673, FI41653, LP00651, SDCCGSBI-0050631.P002, ( inverted question mark)-Ibotenic acid, NCGC00015555-03, NCGC00015555-04, NCGC00015555-05, NCGC00015555-06, NCGC00024524-02, NCGC00024524-03, NCGC00024524-04, NCGC00261336-01, 5-Isoxazoleacetic acid,3-dihydro-3-oxo-, a-Amino-3-hydroxy-5-isoxazoleacetic acid, CS-13243, DA-54220, SMR001230640, SY252217, CAS_2552-55-8, a-Amino-(3-hydroxy-5-isoxazolyl)acetic acid, CS-0020472, EU-0100651, NS00075437, ST50824671, Amino(3-hydroxy-1,2-oxazol-5-yl)acetic acid, I 2765, L000672, Q411094, SR-01000075462-1, SR-01000075462-3, 5-Isoxazoleacetic acid, ?-amino-2,3-dihydro-3-oxo-, BRD-A04628621-001-02-6, 2-Amino-2-(3-oxo-2,3-dihydro-5-isoxazolyl)acetic Acid, 2-amino-2-(3-oxo-2,3-dihydroisoxazol-5-yl)aceticacid, Amino-(3-hydroxy-isoxazol-5-yl)-acetic acid(Ibotenic acid), 2-amino-2-(3-oxo-2,3-dihydro-1,2-oxazol-5-yl)acetic acid, acetic acid, 2-amino-2-(2,3-dihydro-3-oxo-5-isoxazolyl)-, ( inverted question mark)-alpha-Amino-3-hydroxy-5-isoxazoleacetic acid
Theoretical properties:
molecular_formula: C5H6N2O4
molecular_weight: 158.11 g/mol
exact_mass: 158.03275668 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 11
topological_polar_surface_area: 102 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Ibotenic acid is a non-proteinogenic alpha-amino acid. It has a role as a neurotoxin.", "chebi": null, "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Ibotenic acid, or ibotenate, also known as premuscimol or as (S)-2-amino-2-(3-hydroxyisoxazol-5-yl)acetic acid, is a naturally occurring \u03b1-amino acid found in certain Amanita mushrooms such as Amanita muscaria. It acts primarily as a potent glutamate receptor agonist and produces neurological effects. The compound is used as a brain-lesioning agent in scientific research.\nIbotenic acid is a conformationally-restricted analogue of the excitatory neurotransmitter glutamate which acts as a non-selective agonist of glutamate receptors, strongly activating NMDA, group I and II metabotropic glutamate receptors, and weakly activating AMPA and kainate receptors. Taken systemically, it is a prodrug of muscimol, broken down by the liver into this more stable compound, which acts as a potent GABAA and GABAA-\u03c1 receptor agonist. Although the compound's psychoactive effects are not well-understood, some researchers speculate that ibotenic acid itself may have stimulant-like properties. Ibotenic acid is biosynthesized from glutamic acid by hydroxylation catalyzed by an Fe(II)/2-oxoglutarate-dependent oxygenase, with subsequent conversion steps carried out by enzymes encoded within a linked biosynthetic gene cluster.\nIbotenic acid is commonly used in research to create site-specific hippocampal brain lesions in rats, allowing for task relearning due to its interaction with glutamate receptors, and is favored over other agents for its selectivity and long-term stability in saline solution. It induces excitotoxicity in rodents by overactivating NMDA and metabotropic glutamate receptors, leading to calcium overload and oxidative damage.  In contrast, it targets glutamate-gated chloride channels in invertebrates, causing increased chloride permeability without affecting their excitatory glutamate receptors."}