DL-TBOA   Click here for help

GtoPdb Ligand ID: 4631

Synonyms: dl-threo-β-benzyloxyaspartate
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 3
Rotatable bonds 6
Topological polar surface area 109.85
Molecular weight 239.08
XLogP -2.24
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NC(C(C(=O)O)OCc1ccccc1)C(=O)O
Isomeric SMILES N[C@@H]([C@@H](C(=O)O)OCc1ccccc1)C(=O)O
InChI InChI=1S/C11H13NO5/c12-8(10(13)14)9(11(15)16)17-6-7-4-2-1-3-5-7/h1-5,8-9H,6,12H2,(H,13,14)(H,15,16)/t8-,9-/m0/s1
InChI Key BYOBCYXURWDEDS-IUCAKERBSA-N
References
1. Shigeri Y, Shimamoto K, Yasuda-Kamatani Y, Seal RP, Yumoto N, Nakajima T, Amara SG. (2001)
Effects of threo-beta-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5).
J. Neurochem., 79 (2): 297-302. [PMID:11677257]
2. Shimamoto K, Lebrun B, Yasuda-Kamatani Y, Sakaitani M, Shigeri Y, Yumoto N, Nakajima T. (1998)
DL-threo-beta-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters.
Mol. Pharmacol., 53 (2): 195-201. [PMID:9463476]
3. Shimamoto K, Shigeri Y, Yasuda-Kamatani Y, Lebrun B, Yumoto N, Nakajima T. (2000)
Syntheses of optically pure beta-hydroxyaspartate derivatives as glutamate transporter blockers.
Bioorg. Med. Chem. Lett., 10 (21): 2407-10. [PMID:11078189]