Basic information
- Standard SMILES
N[C@@H](CCC(=O)[O-])C(=O)[O-]- InChIKey
WHUUTDBJXJRKMK-VKHMYHEASA-L- Molecular formula
- C5H7NO4-2
- Average molar mass
- 145.11 g/mol
- Monoisotopic mass
- 145.03860486
Overview
L-glutamate(2-) is an L-alpha-amino acid anion that is the dianion obtained by the deprotonation of the both the carboxy groups of L-glutamic acid. It is a glutamate(2-) and a L-alpha-amino acid anion. It is a conjugate base of a L-glutamate(1-). It is an enantiomer of a D-glutamate(2-).
Names & identifiers
- Preferred name
- L-glutamate(2-)
- IUPAC
- (2S)-2-aminopentanedioate
Names & synonyms
L-glutamate(2-)(2S)-2-aminopentanedioateCHEBI:29988RefChem:1088172glutamate(S)-2-Aminopentanedioic acid dianion138-18-1L-glutamic acid dianionL-Glutamic acid (2-)WHUUTDBJXJRKMK-VKHMYHEASA-LDTXSID201315375Q27110357
Database identifiers
- CAS
138-18-1- PubChem CID
- 5460544
- DTXSID
DTXSID201315375- ChEBI
CHEBI:29988- Nikkaji
- J2.338.013G
Properties
Computed structural properties
- XLogP
- -2.4
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- -2
- Complexity
- 134
Safety & regulation
Toxicology
Exposure RoutesAbsorbed from the lumen of the small intestine into the enterocytes.Absorption is efficient and occurs by an active transport mechanism.
Toxicity Summary
Glutamate activates both ionotropic and metabotropic glutamate receptors. The ionotropic ones being non-NMDA (AMPA and kainate) and NMDA receptors. Free glutamic acid cannot cross the blood-brain barrier in appreciable quantities; instead it is converted into L-glutamine, which the brain uses for fuel and protein synthesis. It is conjectured that glutamate is involved in cognitive functions like learning and memory in the brain, though excessive amounts may cause neuronal damage associated in diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. Also, the drug phencyclidine (more commonly known as PCP) antagonizes glutamate at the NMDA receptor, causing behavior reminiscent of schizophrenia. Glutamate in action is extremely difficult to study due to its transient nature.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHepatic
Uses & manufacturing
UsesConsidered to be nature's "Brain food" by improving mental capacities; helps speed the healing of ulcers; gives a "lift" from fatigue; helps control alcoholism, schizophrenia and the craving for sugar.
Related reactions
52 records
Linked notes
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