L-glutamate(2-)

HCID 5460544

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Grundinformationen

CAS: 138-18-1
Standard-SMILES: N[C@@H](CCC(=O)[O-])C(=O)[O-]
InChIKey: WHUUTDBJXJRKMK-VKHMYHEASA-L
Summenformel: C5H7NO4-2
Durchschnittliche Molmasse: 145,11 g/mol
Monoisotopische Masse: 145,03860486

Überblick

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-).

Namen und Bezeichner

Bevorzugter Name: L-glutamate(2-)
IUPAC: (2S)-2-aminopentanedioate

Namen und Synonyme

L-glutamate(2-)(2S)-2-aminopentanedioateCHEBI:29988RefChem:1088172glutamate(S)-2-Aminopentanedioic acid dianion138-18-1L-glutamic acid dianionL-Glutamic acid (2-)WHUUTDBJXJRKMK-VKHMYHEASA-LDTXSID201315375Q27110357

Datenbank-Bezeichner

CAS: 138-18-1
PubChem CID: 5460544
DTXSID: DTXSID201315375
ChEBI: CHEBI:29988
Nikkaji: J2.338.013G

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -2,4
Polarare Oberfläche (TPSA): 106 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 2
Schwere Atome: 10
Formalladung: -2
Komplexität: 134

Sicherheit und Regulatorisches

Toxikologische Informationen

Exposure RoutesAbsorbed from the lumen of the small intestine into the enterocytes.Absorption is efficient and occurs by an active transport mechanism.

Toxicity Summary · 1 Eintrag

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).

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesHepatic

Verwendung und Herstellung

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.