L-AP4   Click here for help

GtoPdb Ligand ID: 1410

Synonyms: L-2-amino-4-phosphonobutiric acid | S-2-amino-4-phosphonobutyrate
PDB Ligand
Compound class: Synthetic organic
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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.

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View interactive charts of activity data across species

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2D Structure
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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.

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Click here for structure editor
Physico-chemical Properties
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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.

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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 130.66
Molecular weight 183.03
XLogP -4.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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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.

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Canonical SMILES OC(=O)C(CCP(=O)(O)O)N
Isomeric SMILES OC(=O)[C@H](CCP(=O)(O)O)N
InChI InChI=1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
InChI Key DDOQBQRIEWHWBT-VKHMYHEASA-N
References
1. Eriksen L, Thomsen C. (1995)
[3H]-L-2-amino-4-phosphonobutyrate labels a metabotropic glutamate receptor, mGluR4a.
Br J Pharmacol, 116 (8): 3279-87. [PMID:8719808]
2. 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]
3. 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]
4. 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]
5. Saugstad JA, Kinzie JM, Shinohara MM, Segerson TP, Westbrook GL. (1997)
Cloning and expression of rat metabotropic glutamate receptor 8 reveals a distinct pharmacological profile.
Mol Pharmacol, 51 (1): 119-25. [PMID:9016353]
6. Tanabe Y, Nomura A, Masu M, Shigemoto R, Mizuno N, Nakanishi S. (1993)
Signal transduction, pharmacological properties, and expression patterns of two rat metabotropic glutamate receptors, mGluR3 and mGluR4.
J Neurosci, 13 (4): 1372-8. [PMID:8463825]
7. Thomas NK, Wright RA, Howson PA, Kingston AE, Schoepp DD, Jane DE. (2001)
(S)-3,4-DCPG, a potent and selective mGlu8a receptor agonist, activates metabotropic glutamate receptors on primary afferent terminals in the neonatal rat spinal cord.
Neuropharmacology, 40 (3): 311-8. [PMID:11166323]
8. 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]
9. 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]
10. 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]