Structure Database (LMSD)
Common Name
Cycloserine
Systematic Name
Synonyms
3D model of Cycloserine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
D-Cycloserine is an NMDA receptor (NMDAR) partial agonist with antibiotic activity. It selectively binds to the glycine binding site (Ki = 2.33 μM) over the glutamate binding site (Ki = >100 μM).1 D-Cycloserine modulates memory in a T-maze footshock test in CD-1 mice with optimal memory retention at doses of 10-30 mg/kg.2 Administration of D-cycloserine (20-40 mg/kg) improves memory retention in ‘senescence-accelerated’ mice which exhibit impaired learning and memory. D-Cycloserine inhibits L-alanine racemase and D-alanine:D-alanine ligase, enzymes essential to peptidoglycan synthesis and bacterial cell wall formation.3 Formulations containing D-cycloserine have been used as second-line agents to treat drug resistant tuberculosis.4
This information has been provided by Cayman Chemical
References
1. Hood, W.F., Compton, R.P., and Monahan, J.B. D-cycloserine: A ligand for the N-methyl-D-aspartate coupled glycine receptor has partial agonist characteristics. Neurosci. Lett. 98(1), 91-95 (1989).
3. Feng, Z., and Barletta, R.G. Roles of Mycobacterium smegmatis D-alanine:D-alanine ligase and D-alanine racemase in the mechanisms of action of and resistance to the peptidoglycan inhibitor D-cycloserine. Antimicrob. Agents Chemother. 47(1), 283-291 (2003).
String Representations
InChiKey (Click to copy)
DYDCUQKUCUHJBH-UWTATZPHSA-N
InChi (Click to copy)
InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
SMILES (Click to copy)
[C@]1([H])(N)CONC1=O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
7
Rings
1
Aromatic Rings
0
Rotatable Bonds
0
Van der Waals Molecular Volume
85.04
Topological Polar Surface Area
66.42
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
2
logP
-1.05
Molar Refractivity
23.07
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Updated at
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