kainate   

GtoPdb Ligand ID: 4231

Comment: Please note that the PubChem entry linked to above refers to the acid form of the compound.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 92.29
Molecular weight 211.08
XLogP -1.18
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES [O-]C(=O)CC1C(CNC1C(=O)[O-])C(=C)C
Isomeric SMILES [O-]C(=O)C[C@H]1[C@H](CN[C@@H]1C(=O)[O-])C(=C)C
InChI InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/p-2/t6-,7+,9-/m0/s1
InChI Key VLSMHEGGTFMBBZ-OOZYFLPDSA-L
References
1. Cantrell BE, Zimmerman DM, Monn JA, Kamboj RK, Hoo KH, Tizzano JP, Pullar IA, Farrell LN, Bleakman D. (1996)
Synthesis of a series of aryl kainic acid analogs and evaluation in cells stably expressing the kainate receptor humGluR6.
J. Med. Chem., 39 (19): 3617-24. [PMID:8809152]
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. Small B, Thomas J, Kemp M, Hoo K, Ballyk B, Deverill M, Ogden AM, Rubio A, Pedregal C, Bleakman D. (1998)
LY339434, a GluR5 kainate receptor agonist.
Neuropharmacology, 37 (10-11): 1261-7. [PMID:9849663]
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]