L-glutamic acid   Click here for help

GtoPdb Ligand ID: 1369

Synonyms: L-Glu | L-glutamate | poly-L-glutamate
PDB Ligand
Compound class: Metabolite or derivative
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: glutamate

L-glutamic acid is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 100.62
Molecular weight 147.05
XLogP -3.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES OC(=O)CCC(C(=O)O)N
Isomeric SMILES OC(=O)CC[C@@H](C(=O)O)N
InChI InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
InChI Key WHUUTDBJXJRKMK-VKHMYHEASA-N
References
1. Ahmadian H, Nielsen B, Bräuner-Osborne H, Johansen TN, Stensbøl TB, Sløk FA, Sekiyama N, Nakanishi S, Krogsgaard-Larsen P, Madsen U. (1997)
(S)-homo-AMPA, a specific agonist at the mGlu6 subtype of metabotropic glutamic acid receptors.
J Med Chem, 40 (22): 3700-5. [PMID:9357538]
2. Boss V, Nutt KM, Conn PJ. (1994)
L-cysteine sulfinic acid as an endogenous agonist of a novel metabotropic receptor coupled to stimulation of phospholipase D activity.
Mol Pharmacol, 45: 1177-1182. [PMID:8022410]
3. Brabet I, Parmentier ML, De Colle C, Bockaert J, Acher F, Pin JP. (1998)
Comparative effect of L-CCG-I, DCG-IV and gamma-carboxy-L-glutamate on all cloned metabotropic glutamate receptor subtypes.
Neuropharmacology, 37 (8): 1043-51. [PMID:9833633]
4. Christopoulos A, Changeux JP, Catterall WA, Fabbro D, Burris TP, Cidlowski JA, Olsen RW, Peters JA, Neubig RR, Pin JP et al.. (2014)
International union of basic and clinical pharmacology. XC. multisite pharmacology: recommendations for the nomenclature of receptor allosterism and allosteric ligands.
Pharmacol Rev, 66 (4): 918-47. [PMID:25026896]
5. Conigrave AD, Quinn SJ, Brown EM. (2000)
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
Proc Natl Acad Sci USA, 97 (9): 4814-9. [PMID:10781086]
6. Fagni L, Chavis P, Ango F, Bockaert J. (2000)
Complex interactions between mGluRs, intracellular Ca2+ stores and ion channels in neurons.
Trends Neurosci, 23 (2): 80-8. [PMID:10652549]
7. Fei YJ, Sugawara M, Nakanishi T, Huang W, Wang H, Prasad PD, Leibach FH, Ganapathy V. (2000)
Primary structure, genomic organization, and functional and electrogenic characteristics of human system N 1, a Na+- and H+-coupled glutamine transporter.
J Biol Chem, 275 (31): 23707-17. [PMID:10823827]
8. Han G, Hampson DR. (1999)
Ligand binding to the amino-terminal domain of the mGluR4 subtype of metabotropic glutamate receptor.
J Biol Chem, 274 (15): 10008-13. [PMID:10187777]
9. Johnson BG, Wright RA, Arnold MB, Wheeler WJ, Ornstein PL, Schoepp DD. (1999)
[3H]-LY341495 as a novel antagonist radioligand for group II metabotropic glutamate (mGlu) receptors: characterization of binding to membranes of mGlu receptor subtype expressing cells.
Neuropharmacology, 38 (10): 1519-29. [PMID:10530814]
10. Laurie DJ, Schoeffter P, Wiederhold KH, Sommer B. (1997)
Cloning, distribution and functional expression of the human mGlu6 metabotropic glutamate receptor.
Neuropharmacology, 36 (2): 145-52. [PMID:9144651]
11. Lavreysen H, Janssen C, Bischoff F, Langlois X, Leysen JE, Lesage AS. (2003)
[3H]R214127: a novel high-affinity radioligand for the mGlu1 receptor reveals a common binding site shared by multiple allosteric antagonists.
Mol Pharmacol, 63 (5): 1082-93. [PMID:12695537]
12. Malherbe P, Kratzeisen C, Lundstrom K, Richards JG, Faull RL, Mutel V. (1999)
Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.
Brain Res Mol Brain Res, 67 (2): 201-10. [PMID:10216218]
13. Miyaji T, Omote H, Moriyama Y. (2011)
Functional characterization of vesicular excitatory amino acid transport by human sialin.
J Neurochem, 119 (1): 1-5. [PMID:21781115]
14. Mutel V, Ellis GJ, Adam G, Chaboz S, Nilly A, Messer J, Bleuel Z, Metzler V, Malherbe P, Schlaeger EJ et al.. (2000)
Characterization of [(3)H]Quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections.
J Neurochem, 75 (6): 2590-601. [PMID:11080213]
15. Pin JP, De Colle C, Bessis AS, Acher F. (1999)
New perspectives for the development of selective metabotropic glutamate receptor ligands.
Eur J Pharmacol, 375 (1-3): 277-94. [PMID:10443583]
16. Schweitzer C, Kratzeisen C, Adam G, Lundstrom K, Malherbe P, Ohresser S, Stadler H, Wichmann J, Woltering T, Mutel V. (2000)
Characterization of [(3)H]-LY354740 binding to rat mGlu2 and mGlu3 receptors expressed in CHO cells using semliki forest virus vectors.
Neuropharmacology, 39 (10): 1700-6. [PMID:10884552]
17. Thomsen C, Kristensen P, Mulvihill E, Haldeman B, Suzdak PD. (1992)
L-2-amino-4-phosphonobutyrate (L-AP4) is an agonist at the type IV metabotropic glutamate receptor which is negatively coupled to adenylate cyclase.
Eur J Pharmacol, 227 (3): 361-2. [PMID:1361913]
18. Thomsen C, Pekhletski R, Haldeman B, Gilbert TA, O'Hara P, Hampson DR. (1997)
Cloning and characterization of a metabotropic glutamate receptor, mGluR4b.
Neuropharmacology, 36 (1): 21-30. [PMID:9144638]
19. Wright RA, Arnold MB, Wheeler WJ, Ornstein PL, Schoepp DD. (2000)
Binding of [3H](2S,1'S,2'S)-2-(9-xanthylmethyl)-2-(2'-carboxycyclopropyl) glycine ([3H]LY341495) to cell membranes expressing recombinant human group III metabotropic glutamate receptor subtypes.
Naunyn Schmiedebergs Arch Pharmacol, 362 (6): 546-54. [PMID:11138847]
20. Wu S, Wright RA, Rockey PK, Burgett SG, Arnold JS, Rosteck Jr PR, Johnson BG, Schoepp DD, Belagaje RM. (1998)
Group III human metabotropic glutamate receptors 4, 7 and 8: molecular cloning, functional expression, and comparison of pharmacological properties in RGT cells.
Brain Res Mol Brain Res, 53 (1-2): 88-97. [PMID:9473604]