Aspartic acid
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Names |
IUPAC names
Trivial: Aspartic acid
Systematic: 2-Aminobutanedioic acid
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Other names
Aminosuccinic acid, asparagic acid, asparaginic acid[1]
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Identifiers |
CAS Registry Number
|
617-45-8 Y
56-84-8 (L-isomer) N
1783-96-6 (D-isomer) N |
ChEBI |
CHEBI:22660 Y |
ChEMBL |
ChEMBL139661 Y |
ChemSpider |
411 Y |
EC-number |
200-291-6 |
InChI
-
InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) Y
Key: CKLJMWTZIZZHCS-UHFFFAOYSA-N Y
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InChI=1/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)
Key: CKLJMWTZIZZHCS-UHFFFAOYAE
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Jmol-3D images |
Image
Image |
KEGG |
C16433 Y |
PubChem |
424 |
SMILES
-
O=C(O)CC(N)C(=O)O
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C(C(C(=O)O)N)C(=O)O
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UNII |
28XF4669EP Y |
Properties |
Molecular formula
|
C4H7NO4 |
Molar mass |
133.10 g·mol−1 |
Appearance |
colourless crystals |
Density |
1.7 g/cm3 |
Melting point |
270 °C (518 °F; 543 K) |
Boiling point |
324 °C (615 °F; 597 K) (decomposes) |
Solubility in water
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4.5 g/L [2] |
Acidity (pKa) |
3.9 |
Hazards |
MSDS |
External MSDS |
EU Index |
not listed |
NFPA 704 |
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Supplementary data page |
Structure and
properties
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Refractive index (n),
Dielectric constant (εr), etc. |
Thermodynamic
data
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Phase behaviour
solid–liquid–gas |
Spectral data
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UV, IR, NMR, MS |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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N verify (what is: Y/N?) |
Infobox references |
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Aspartic acid (abbreviated as Asp or D)[3] is an α-amino acid with the chemical formula HOOCCH(NH2)CH2COOH. The carboxylate anion and salts of aspartic acid are known as aspartate. The L-isomer of aspartate is one of the 23 proteinogenic amino acids, i.e., the building blocks of proteins. Its codons are GAU and GAC.
Aspartic acid is, together with glutamic acid, classified as an acidic amino acid with a pKa of 3.9, however in a peptide the pKa is highly dependent on the local environment. A pKa as high as 14 is not at all uncommon. Aspartate is pervasive in biosynthesis. As with all amino acids, the presence of acid protons depends on the residue's local chemical environment and the pH of the solution.
Contents
- 1 Discovery
- 2 Forms and nomenclature
- 3 Role in biosynthesis of amino acids
- 4 Other biochemical roles
- 4.1 Interactive pathway map
- 4.2 Neurotransmitter
- 5 Sources
- 5.1 Dietary sources
- 5.2 Chemical synthesis
- 6 See also
- 7 References
- 8 External links
Discovery
Aspartic acid was first discovered in 1827 by Plisson, derived from asparagine, which had been isolated from asparagus juice in 1806, by boiling with a base.[4]
Forms and nomenclature
There are two forms or enantiomers of aspartic acid. The name "aspartic acid" can refer to either enantiomer or a mixture of two.[3] Of these two forms, only one, "L-aspartic acid", is directly incorporated into proteins. The biological roles of its counterpart, "D-aspartic acid" are more limited. Where enzymatic synthesis will produce one or the other, most chemical syntheses will produce both forms, "DL-aspartic acid," known as a racemic mixture.
Role in biosynthesis of amino acids
Aspartate is non-essential in mammals, being produced from oxaloacetate by transamination. It can also be generated from ornithine and citrulline in the urea cycle. In plants and microorganisms, aspartate is the precursor to several amino acids, including four that are essential for humans: methionine, threonine, isoleucine, and lysine. The conversion of aspartate to these other amino acids begins with reduction of aspartate to its "semialdehyde," O2CCH(NH2)CH2CHO.[5] Asparagine is derived from aspartate via transamidation:
- -O2CCH(NH2)CH2CO2- + GC(O)NH3+ O2CCH(NH2)CH2CONH3+ + GC(O)O
(where GC(O)NH2 and GC(O)OH are glutamine and glutamic acid, respectively)
Other biochemical roles
Aspartate is also a metabolite in the urea cycle and participates in gluconeogenesis. It carries reducing equivalents in the malate-aspartate shuttle, which utilizes the ready interconversion of aspartate and oxaloacetate, which is the oxidized (dehydrogenated) derivative of malic acid. Aspartate donates one nitrogen atom in the biosynthesis of inosine, the precursor to the purine bases. In addition, aspartic acid acts as hydrogen acceptor in a chain of ATP synthase.
Interactive pathway map
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
[[File:
|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit|]]
File:WP534.png
Glycolysis and Gluconeogenesis edit
- ^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".
Neurotransmitter
Aspartate (the conjugate base of aspartic acid) stimulates NMDA receptors, though not as strongly as the amino acid neurotransmitter L-glutamate does.[6]
Sources
Dietary sources
Aspartic acid is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans. Aspartic acid is found in:
- Animal sources: oysters, luncheon meats, sausage meat, wild game
- Vegetable sources: sprouting seeds, oat flakes, avocado, asparagus[citation needed], young sugarcane, and molasses from sugar beets.[1]
- Dietary supplements, either as aspartic acid itself or salts (such as magnesium aspartate)
- The sweetener aspartame (brands: NutraSweet, Equal, Canderel, etc.)
Chemical synthesis
Racemic aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, (C6H4(CO)2NC(CO2Et)2).[7]
The major disadvantage of the above technique is that equimolar amounts of each enantiomer are made. Using biotechnology it is now possible to use immobilised enzymes to create just one type of enantiomer owing to their stereospecificity. Aspartic acid is made synthetically using ammonium fumarate and aspartase from E.coli, E.coli usually breaks down the aspartic acid as a nitrogen source but using excess amounts of ammonium fumarate a reversal of the enzyme's job is possible, and so aspartic acid is made to very high yields, 98.7 mmol from 1 mol.
See also
- Aspartate transaminase
- Polyaspartic acid
- Sodium poly(aspartate), a synthetic polyamide
References
- ^ a b "862. Aspartic acid". The Merck Index (11th ed.). 1989. p. 132. ISBN 0-911910-28-X.
- ^ http://www.inchem.org/documents/icsc/icsc/eics1439.htm
- ^ a b "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem. 56 (5), 1984: 595–624, doi:10.1351/pac198456050595 .
- ^ R.H.A. Plimmer (1912) [1908]. R.H.A. Plimmer & F.G. Hopkins, ed. The chemical composition of the proteins. Monographs on biochemistry. Part I. Analysis (2nd ed.). London: Longmans, Green and Co. p. 112. Retrieved January 18, 2010.
- ^ Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2000), Principles of Biochemistry (3rd ed.), New York: W. H. Freeman, ISBN 1-57259-153-6 .
- ^ Chen, Philip E.; Geballe, Matthew T.; Stansfeld, Phillip J.; Johnston, Alexander R.; Yuan, Hongjie; Jacob, Amanda L.; Snyder, James P.; Traynelis, Stephen F.; Wyllie, David J. A. (2005). "Structural Features of the Glutamate Binding Site in Recombinant NR1/NR2A N-Methyl-D-aspartate Receptors Determined by Site-Directed Mutagenesis and Molecular Modeling". Mol. Pharmacol. 67 (5): 1470–84. doi:10.1124/mol.104.008185. PMID 15703381.
- ^ Dunn, M. S.; Smart, B. W. (1950). "DL-Aspartic Acid". Org. Synth. 30: 7. ; Coll. Vol. 4, p. 55 .
External links
- GMD MS Spectrum
- American Chemical Society (21 April 2010). "Ancestral Eve' Crystal May Explain Origin of Life's Left-Handedness". ScienceDaily. Archived from the original on 23 April 2010. Retrieved 2010-04-21.
Other hematological agents
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Antianemic
preparations
(B03) |
Erythropoietins
|
- Darbepoetin alfa
- Methoxy polyethylene glycol-epoetin beta
- Peginesatide
|
|
Iron supplements
|
- Ferrous ascorbate
- Ferrous aspartate
- Ferrous carbonate
- Ferrous chloride
- Ferrous fumarate
- Ferrous gluconate
- Ferrous glycine sulfate
- Ferrous iodine
- Ferrous succinate
- Ferrous sulfate
- Ferrous tartrate
- Iron sucrose
- Sodium ferric gluconate complex
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|
|
Blood
substitutes and
perfusion solutions
(B05) |
- Dextran
- Gelatin agents
- Hemoglobin crosfumaril
- Hemoglobin raffimer
- Hydroxyethyl starch
- Icodextrin
- Mannitol
- Serum albumin
- Sorbitol
|
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Enzymes
(B06AA) |
- Bromelain
- Chymotrypsin
- Deoxyribonuclease
- Fibrinolysin
- Hyaluronidase
- Streptokinase
- Trypsin
|
|
Drugs used in
hereditary
angioedema
(B06AC) |
- C1-inhibitor
- Conestat alfa
- Ecallantide
- Icatibant
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|
Index of cells from bone marrow
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|
Description |
- Immune system
- Cells
- Physiology
- coagulation
- proteins
- granule contents
- colony-stimulating
- heme and porphyrin
|
|
Disease |
- Red blood cell
- Monocyte and granulocyte
- Neoplasms and cancer
- Histiocytosis
- Symptoms and signs
- Blood tests
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|
Treatment |
- Transfusion
- Drugs
- thrombosis
- bleeding
- other
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The encoded amino acid
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|
General topics |
- Protein
- Peptide
- Genetic code
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|
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By properties |
Aliphatic
|
- Branched-chain amino acids (Valine
- Isoleucine
- Leucine)
- Methionine
- Alanine
- Proline
- Glycine
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Aromatic
|
- Phenylalanine
- Tyrosine
- Tryptophan
- Histidine
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Polar, uncharged
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- Asparagine
- Glutamine
- Serine
- Threonine
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Positive charge (pKa)
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- Lysine (≈10.8)
- Arginine (≈12.5)
- Histidine (≈6.1)
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Negative charge (pKa)
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- Aspartic acid (≈3.9)
- Glutamic acid (≈4.1)
- Cysteine (≈8.3)
- Tyrosine (≈10.1)
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|
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Other classifications |
- Essential amino acid
- Ketogenic amino acid
- Glucogenic amino acid
- Non-proteinogenic amino acid
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Index of biochemical families
|
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
|
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
- Tetrapyrroles
- intermediates
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Neurotransmitters
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Amino acid-derived |
- Major excitatory/inhibitory systems: Glutamate system: Agmatine
- Aspartic acid (aspartate)
- Cycloserine
- Glutamic acid (glutamate)
- Glycine
- Kynurenic acid
- NAA
- NAAG
- Serine; GABA system: GABA
- GABOB
- Proline; Glycine system: β-Alanine
- Alanine
- Glycine
- Hypotaurine
- Proline
- Sarcosine
- Serine
- Taurine; GHB system: GHB
- T-HCA
- Biogenic amines: Monoamines: Dopamine
- Epinephrine (adrenaline)
- Histamine
- Melatonin
- NAS (normelatonin)
- Norepinephrine (noradrenaline)
- Serotonin (5-HT); Trace amines:
- 3-Iodothyronamine
- N-Methylphenethylamine
- N-Methyltryptamine
- m-Octopamine
- p-Octopamine
- Phenylethanolamine
- Phenethylamine
- Synephrine
- Tryptamine
- m-Tyramine
- p-Tyramine
- Neuropeptides: See here instead.
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Lipid-derived |
- Endocannabinoids: 2-AG
- 2-AGE (noladin ether)
- 2-OG
- AA-5-HT
- Anandamide (AEA)
- DEA
- LPI
- NADA
- NAGly
- OEA
- Oleamide
- PEA
- SEA
- Virodhamine (OAE)
- Neurosteroids: See here instead.
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Nucleobase-derived |
- Nucleosides: Adenosine system: Adenosine
- ADP
- AMP
- ATP
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Vitamin-derived |
- Cholinergic system: Acetylcholine
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Miscellaneous |
- Gasotransmitters: Carbon monoxide (CO)
- Hydrogen sulfide (H2S)
- Nitrous oxide (NO); Candidates: Acetaldehyde
- Ammonia (NH3)
- Carbonyl sulfide (COS)
- Nitrous oxide (N2O)
- Sulfur dioxide (SO2)
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Index of the peripheral nervous system
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|
Description |
- Anatomy
- Nerves
- cranial
- trigeminal
- cervical
- brachial
- lumbosacral plexus
- somatosensory
- spinal
- autonomic
- Physiology
- reflexes
- proteins
- neurotransmitters
- transporters
- Development
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Disease |
- Autonomic
- Congenital
- Injury
- Neoplasms and cancer
- Other
- Symptoms and signs
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Treatment |
- Procedures
- Local anesthetics
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Glutamatergics
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Receptor
(ligands) |
AMPA |
- Agonists: Glutamate/active site agonists: 5-Fluorowillardiine
- Acromelic acid (acromelate)
- AMPA
- BOAA
- Domoic acid
- Glutamate
- Ibotenic acid
- Proline
- Quisqualic acid
- Willardiine; Positive allosteric modulators: Aniracetam
- Cyclothiazide
- CX-516
- CX-546
- CX-614
- Farampator (CX-691, Org 24448)
- CX-717
- CX-1739
- CX-1942
- Diazoxide
- Hydrochlorothiazide (HCTZ)
- IDRA-21
- LY-392,098
- LY-404,187
- LY-451,646
- LY-503,430
- Mibampator (LY-451,395)
- Org 26576
- Oxiracetam
- PEPA
- Piracetam
- Pramiracetam
- S-18986
- Sunifiram
- Unifiram
- Antagonists: ACEA-1011
- ATPO
- Becampanel
- Caroverine
- CNQX
- Dasolampanel
- DNQX
- Fanapanel (MPQX)
- GAMS
- GYKI-52466
- Kynurenic acid
- Licostinel (ACEA-1021)
- NBQX
- PNQX
- Selurampanel
- Tezampanel
- Theanine
- Topiramate
- YM90K
- Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
- Cyclopropane
- Enflurane
- Ethanol
- Evans blue
- GYKI-53,655
- Halothane
- Irampanel
- Isoflurane
- Perampanel
- Pregnenolone sulfate
- Talampanel
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NMDA |
- Agonists: Glutamate/active site agonists: AMAA
- Aspartate
- Glutamate
- Homocysteic acid (L-HCA)
- Homoquinolinic acid
- Ibotenic acid
- NMDA
- Proline
- Quinolinic acid
- Tetrazolylglycine
- Theanine; Glycine site agonists: β-Fluoro-D-alanine
- ACBD
- ACC (ACPC)
- ACPD
- CCG
- D-Alanine
- D-Cycloserine
- D-Serine
- DHPG
- Glycine
- HA-966
- L-687,414
- L-Alanine
- L-Serine
- Milacemide
- NRX-1074
- Rapastinel (GLYX-13)
- Sarcosine; Polyamine site agonists: Spermidine
- Spermine
- Antagonists: Competitive antagonists: AP5 (APV)
- AP7
- CGP-37849
- CGP-39551
- CGP-39653
- CGP-40116
- CGS-19755
- CPP
- LY-233,053
- LY-235,959
- LY-274,614
- MDL-100,453
- Midafotel (d-CPPene)
- NPC-12,626
- NPC-17,742
- PBPD
- PEAQX
- Perzinfotel
- PPDA
- SDZ-220581
- Selfotel; Noncompetitive antagonists: ARR-15,896
- Caroverine
- Dexanabinol
- FPL-12495
- FR-115,427
- Hodgkinsine
- Magnesium
- MDL-27,266
- NPS-1506
- Psychotridine
- Zinc; Uncompetitive pore blockers: 2-MDP
- 3-MeO-PCP
- 8A-PDHQ
- 18-MC
- α-Endopsychosin
- Alaproclate
- Amantadine
- Aptiganel
- ARL-12,495
- ARL-15,896-AR
- ARL-16,247
- Budipine
- Conaridine
- Delucemine
- Dexoxadrol
- Dextrallorphan
- Dieticyclidine
- Dizocilpine
- Esketamine
- Etoxadrol
- Eticyclidine
- Gacyclidine
- Ibogaine
- Ibogamine
- Indantadol
- Ketamine
- Ketobemidone
- Lanicemine
- Loperamide
- Memantine
- Methadone (Levomethadone)
- Methorphan (Dextromethorphan
- Levomethorphan)
- Methoxetamine
- Methoxphenidine
- Milnacipran
- Morphanol (Dextrorphan
- Levorphanol)
- NEFA
- Neramexane
- Nitromemantine
- Nitrous oxide
- Noribogaine
- Orphenadrine
- PCPr
- Pethidine (meperidine)
- Phencyclamine
- Phencyclidine
- Propoxyphene
- Remacemide
- Rhynchophylline
- Rimantadine
- Rolicyclidine
- Sabeluzole
- Tabernanthine
- Tenocyclidine
- Tiletamine
- Tramadol
- Xenon; Glycine site antagonists: 7-CKA
- ACC
- ACEA-1011
- ACEA-1328
- AV-101
- Carisoprodol
- CGP-39653
- CNQX
- DCKA
- DNQX
- Felbamate
- Gavestinel
- GV-196,771
- Kynurenic acid
- L-689,560
- L-701,324
- Licostinel (ACEA-1021)
- LU-73,068
- MDL-105,519
- Meprobamate
- MRZ 2/576
- PNQX
- ZD-9379; NR2B subunit antagonists: Besonprodil
- CERC-301 (MK-0657)
- CO-101,244 (PD-174,494)
- Eliprodil
- Haloperidol
- Ifenprodil
- Isoxsuprine
- Nylidrin
- Ro8-4304
- Ro25-6981
- Traxoprodil; Polyamine site antagonists: Arcaine
- Co 101676
- Diaminopropane
- Diethylenetriamine
- Huperzine A
- Putrescine
- Ro 25-6981; Unclassified/unsorted antagonists: Bumetanide
- Chloroform
- Cyclopropane
- D-αAA
- Diethyl ether
- Diphenidine
- Enflurane
- Ethanol
- Flufenamic acid
- Flupirtine
- Furosemide
- Halothane
- Isoflurane
- Metaphit
- Methoxyflurane
- Niflumic acid
- Piretanide
- Toluene
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- Xylene
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|
Kainate |
- Agonists: Glutamate/active site agonists: 5-Bromowillardiine
- 5-Iodowillardiine
- Acromelic acid (acromelate)
- AMPA
- ATPA
- Domoic acid
- Glutamate
- Ibotenic acid
- Kainic acid
- LY-339,434
- Proline
- Quisqualic acid
- SYM-2081; Positive allosteric modulators: Cyclothiazide
- Diazoxide
- Enflurane
- Halothane
- Isoflurane
- Antagonists: ACEA-1011
- CNQX
- Dasolampanel
- DNQX
- GAMS
- Kynurenic acid
- Licostinel (ACEA-1021)
- LY-382,884
- NBQX
- NS102
- Selurampanel
- Tezampanel
- Theanine
- Topiramate
- UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
- Enflurane
- Ethanol
- Evans blue
- NS-3763
- Pregnenolone sulfate
|
|
mGlu1 |
- Agonists: ACPD
- DHPG
- Glutamate
- Ibotenic acid
- Quisqualic acid
- Ro01-6128
- Ro67-4853
- Ro67-7476
- VU-71
- Antagonists: BAY 36-7620
- CPCCOEt
- LY-367,385
- LY-456,236
- MCPG
- NPS-2390
|
|
mGlu2 |
- Agonists: BINA
- CBiPES
- DCG-IV
- Eglumegad
- Glutamate
- Ibotenic acid
- LY-379,268
- LY-404,039
- LY-487,379
- LY-566,332
- MGS-0028; Positive allosteric modulators: JNJ-40411813 (ADX-71149)
- Antagonists: APICA
- CECXG
- EGLU
- HYDIA
- LY-307,452
- LY-341,495
- MCPG
- MGS-0039
- PCCG-4; Negative allosteric modulators: Decoglurant
- RO4491533
|
|
mGlu3 |
- Agonists: CBiPES
- DCG-IV
- Eglumegad
- Glutamate
- Ibotenic acid
- LY-379,268
- LY-404,039
- LY-487,379
- MGS-0028
- Antagonists: APICA
- CECXG
- EGLU
- HYDIA
- LY-307,452
- LY-341,495
- MCPG
- MGS-0039; Negative allosteric modulators: Decoglurant
- RO4491533
|
|
mGlu4 |
- Agonists: Glutamate
- L-AP4
- PHCCC
- VU-001,171
- VU-0155,041; Positive allosteric modulators: MPEP
- Antagonists: CPPG
- MAP4
- MPPG
- MSOP
- MTPG
- UBP-1112
|
|
mGlu5 |
- Agonists: ACPD
- ADX-47273
- CDPPB
- CHPG
- DFB
- DHPG
- Glutamate
- Ibotenic acid
- Quisqualic acid
- VU-1545
- Antagonists: CTEP
- DMeOB
- LY-344,545
- Mavoglurant
- MCPG
- NPS-2390
- SIB-1757
- SIB-1893; Negative allosteric modulators: Basimglurant
- Dipraglurant
- Fenobam
- GRN-529
- MPEP
- MTEP
- Raseglurant
|
|
mGlu6 |
- Agonists: Glutamate
- L-AP4
- Antagonists: CPPG
- MAP4
- MPPG
- MSOP
- MTPG
- UBP-1112
|
|
mGlu7 |
- Agonists: AMN082
- Glutamate
- L-AP4
- Antagonists: CPPG
- MAP4
- MMPIP
- MPPG
- MSOP
- MTPG
- UBP-1112
|
|
mGlu8 |
- Agonists: DCPG
- Glutamate
- L-AP4
- Antagonists: CPPG
- MAP4
- MPPG
- MSOP
- MTPG
- UBP-1112
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|
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Transporter
(blockers) |
EAATs |
- Amphetamine
- Aspartic acid (aspartate)
- cis-ACBD
- DHKA
- Glutamic acid (glutamate)
- HIP-A
- HIP-B
- Kainic acid
- L-(-)-threo-3-Hydroxyaspartic acid
- L-αAA
- L-CCG-III ((2S,3S,4R)-CCG)
- L-Serine-O-sulphate (SOS)
- L-trans-2,4-PDC
- MPDC
- SYM-2081
- TBOA
- TFB-TBOA
- Theanine
- threo-3-Methylglutamic acid
- UCPH-101
- WAY-213,613
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|
vGluTs |
- 4-Methylene-L-glutamate
- 6-(4'-Phenylstyryl)-QDC
- 6-Biphenyl-4-yl-QDC
- 7-CKA
- Acid red 114
- Amido black 10B (naphthol blue black)
- Bafilomycin A1
- Benzopurpurin 4B
- Bumetamide
- Chicago sky blue 6B
- Aspartic acid (aspartate)
- DIDS
- Direct blue 71
- Erythro-4-methyl-L-glutamic acid
- Evans blue
- Furosemide
- Glutamic acid (glutamate)
- Kynurenic acid
- Nigericin
- NPPB (N144)
- Ponceau SS
- Reactive blue 2
- Rose bengal
- SITS
- trans-ACDP
- Trypan blue
- Valinomycin
- Xanthurenic acid
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Enzyme
(inhibitors) |
GAH |
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AST |
- 2-Amino-3-butenoic acid
- AAOA
- AMB
- β-DL-Methylene-aspartate
- Hydrazinosuccinate
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ALT |
- β-Chloro-L-alanine
- L-Cycloserine
- Propargylglycine
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GDH |
- AAOA
- Bithionol
- Chloroquine
- EGCG
- GTP
- GW5074
- Hexachlorophene
- Hydroxylamine
- Palmitoyl-CoA
- Pyridoxal phosphate
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GS |
- 2-Aminoadipic acid
- JFD01307SC
- Methionine sulfoximine
- Phosphinothricin (glufosinate)
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GAD |
- 3-Mercaptopropionic acid
- AAOA
- L-Allylglycine
- Semicarbazide
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Others |
- Precursors: GHB
- L-Glutamine
- Cofactors: α-Ketoglutaric acid
- Iron
- Sulfur
- Vitamin B2
- Vitamin B3
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See also: GABAergics • GHBergics • Glycinergics
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