SYM2081   

GtoPdb Ligand ID: 4317

Synonyms: (2S,4R)-Me-Glu [2] | compound 52 [PMID: 10821708] | SYM 2081 | SYM-2081
Compound class: Synthetic organic
Comment: SYM2081 is a potent agonist of the kainate receptors GluK1 and GluK2 (formerly GluR5 and GluR6) [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 106.28
Molecular weight 159.05
XLogP -4.02
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES [O-]C(=O)C(CC(C(=O)[O-])N)C
Isomeric SMILES [O-]C(=O)[C@@H](C[C@@H](C(=O)[O-])N)C
InChI InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/p-2/t3-,4+/m1/s1
InChI Key KRKRAOXTGDJWNI-DMTCNVIQSA-L
References
1. Pedregal C, Collado I, Escribano A, Ezquerra J, Domínguez C, Mateo AI, Rubio A, Baker SR, Goldsworthy J, Kamboj RK et al.. (2000)
4-Alkyl- and 4-cinnamylglutamic acid analogues are potent GluR5 kainate receptor agonists.
J. Med. Chem., 43 (10): 1958-68. [PMID:10821708]
2. Sagot E, Pickering DS, Pu X, Umberti M, Stensbøl TB, Nielsen B, Chapelet M, Bolte J, Gefflaut T, Bunch L. (2008)
Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7.
J. Med. Chem., 51 (14): 4093-103. [PMID:18578478]
3. Vandenberg RJ, Mitrovic AD, Chebib M, Balcar VJ, Johnston GA. (1997)
Contrasting modes of action of methylglutamate derivatives on the excitatory amino acid transporters, EAAT1 and EAAT2.
Mol. Pharmacol., 51 (5): 809-15. [PMID:9145919]
4. Zhou LM, Gu ZQ, Costa AM, Yamada KA, Mansson PE, Giordano T, Skolnick P, Jones KA. (1997)
(2S,4R)-4-methylglutamic acid (SYM 2081): a selective, high-affinity ligand for kainate receptors.
J. Pharmacol. Exp. Ther., 280 (1): 422-7. [PMID:8996224]