domoic acid   Click here for help

GtoPdb Ligand ID: 4181

Synonyms: domoate | NSC 288031
PDB Ligand
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 123.93
Molecular weight 311.14
XLogP -0
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OC(=O)CC1C(CNC1C(=O)O)C(=CC=CC(C(=O)O)C)C
Isomeric SMILES OC(=O)C[C@H]1[C@H](CN[C@@H]1C(=O)O)/C(=C\C=C\[C@H](C(=O)O)C)/C
InChI InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1
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]