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Chemical substance record

LY 379268

191471-52-0C₇H₉NO₅187.151 g/mol

Organic/Inorganic Small MoleculeChEBI source record

An organic heterobicyclic compound that is (1R,5S)-2-oxabicyclo[3.1.0]hexane carrying amino, carboxy, and carboxy groups at positions 4R, 4R and 6R, respectively. It is a potent agonist of group II metabotropic glutamate receptors mGluR2 and mGluR3 (EC50 = 2.69 nM and 4.48 nM, respectively) that exhibits antipsychotic-like action in animal models of schizophrenia. — ChEBI

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Identity & molecular properties

Source-linked values

CAS number	191471-52-0	ChEBI ↗
Molecular formula	C₇H₉NO₅	ChEBI ↗
Molar mass	187.151 g/mol	ChEBI ↗
Monoisotopic mass	187.04807 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:192545	ChEBI ↗

Names & structural identifiers

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Source preferred name

LY 379268

IUPAC name

(1R,4R,5S,6R)-4-amino-2-oxabicyclo[3.1.0]hexane-4,6-dicarboxylic acid

InChIKey

YASVRZWVUGJELU-MDASVERJSA-N

SMILES

[H][C@@]12[C@@H](C(=O)O)[C@]1([H])OC[C@@]2(N)C(=O)O

InChI

InChI=1S/C7H9NO5/c8-7(6(11)12)1-13-4-2(3(4)7)5(9)10/h2-4H,1,8H2,(H,9,10)(H,11,12)/t2-,3-,4+,7+/m1/s1

Names & synonyms

(1R,4R,5S,6R)-4-amino-2-oxabicyclo[3.1.0]hexane-4,6-dicarboxylic acid

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

organic heterobicyclic compoundChEBI parent class · 27171 ↗bridged compoundChEBI parent class · 35990 ↗amino dicarboxylic acidChEBI parent class · 36164 ↗

carboxylic acid amino acid organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

anxiolytic drugantipsychotic agentmetabotropic glutamate receptor agonistneuroprotective agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00534328 mol

Uses 187.151 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 7 atoms

44.92%

O

Oxygen · 5 atoms

42.74%

N

Nitrogen · 1 atom

7.48%

H

Hydrogen · 9 atoms

4.85%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Synthesis, pharmacological characterization, and molecular modeling of heterobicyclic amino acids related to (+)-2-aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid (LY354740): identification of two new potent, selective, and systemically active agonists for group II metabotropic glutamate receptors. ↗Journal of medicinal chemistry · 1999 Mar 25 · PMID 10090786

Postsynaptic and presynaptic group II metabotropic glutamate receptor activation reduces neuronal excitability in rat midline paraventricular thalamic nucleus. ↗The Journal of pharmacology and experimental therapeutics · 2011 Mar · PMID 21139059

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:192545

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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