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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2D Structure
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Physico-chemical Properties
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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
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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
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]