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ID: ALA475341
Max Phase: Preclinical
Molecular Formula: C11H13NO5
Molecular Weight: 239.23
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: NC(C(=O)O)C(OCc1ccccc1)C(=O)O
Standard 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)
Standard InChI Key: BYOBCYXURWDEDS-UHFFFAOYSA-N
Associated Targets(Human)
SLC1A3 Tchem Excitatory amino acid transporter 1 (586 Activities)
SLC1A2 Tchem Excitatory amino acid transporter 2 (552 Activities)
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SLC1A1 Tchem Excitatory amino acid transporter 3 (527 Activities)
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Associated Targets(non-human)
Glutamate transporter homolog (3 Activities)
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Slc1a6 Excitatory amino acid transporter 4 (71 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 239.23 | Molecular Weight (Monoisotopic): 239.0794 | AlogP: 0.07 | #Rotatable Bonds: 6 |
| Polar Surface Area: 109.85 | Molecular Species: ZWITTERION | HBA: 4 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 2.97 | CX Basic pKa: 8.97 | CX LogP: -2.08 | CX LogD: -5.13 |
| Aromatic Rings: 1 | Heavy Atoms: 17 | QED Weighted: 0.65 | Np Likeness Score: 0.31 |
References
| 1. 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., 10 (21): [PMID:11078189] [10.1016/s0960-894x(00)00487-x] |
| 2. Boudker O, Ryan RM, Yernool D, Shimamoto K, Gouaux E.. (2007) Coupling substrate and ion binding to extracellular gate of a sodium-dependent aspartate transporter., 445 (7126): [PMID:17230192] [10.1038/nature05455] |
| 3. Jensen AA, Erichsen MN, Nielsen CW, Stensbøl TB, Kehler J, Bunch L.. (2009) Discovery of the first selective inhibitor of excitatory amino acid transporter subtype 1., 52 (4): [PMID:19161278] [10.1021/jm8013458] |
| 4. Sagot E, Jensen AA, Pickering DS, Pu X, Umberti M, Stensbøl TB, Nielsen B, Assaf Z, Aboab B, Bolte J, Gefflaut T, Bunch L.. (2008) Chemo-enzymatic synthesis of (2S,4R)-2-amino-4-(3-(2,2-diphenylethylamino)-3-oxopropyl)pentanedioic acid: a novel selective inhibitor of human excitatory amino acid transporter subtype 2., 51 (14): [PMID:18578477] [10.1021/jm800091e] |
| 5. Liu N,Jensen AA,Bunch L. (2020) β-Indolyloxy Functionalized Aspartate Analogs as Inhibitors of the Excitatory Amino Acid Transporters (EAATs)., 11 (11): [PMID:33214831] [10.1021/acsmedchemlett.0c00342] |
Source
Source(1):