L-glutamate(2-)

HCID 5460544CAS 138-18-1

기본 정보

표준 SMILES: N[C@@H](CCC(=O)[O-])C(=O)[O-]
InChIKey: WHUUTDBJXJRKMK-VKHMYHEASA-L
분자식: C5H7NO4-2
평균 분자량: 145.11 g/mol
단동위원소 질량: 145.03860486

개요

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-).

이름 및 식별자

우선 이름: L-glutamate(2-)
IUPAC: (2S)-2-aminopentanedioate

이름 및 동의어

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: -2.4
극성 표면적: 106 Å²
수소 결합 공여자 수: 1
수소 결합 수용자 수: 5
회전 가능 결합 수: 2
무거운 원자 수: 10
형식 전하: -2
복잡도: 134

안전 및 규제

독성 정보

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

Toxicity Summary · 1건

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).

화학 및 산업

약리 정보

Metabolism/MetabolitesHepatic

용도 및 제조

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.