D-cycloserine   Click here for help

GtoPdb Ligand ID: 9489

Synonyms: Seromycin®
Approved drug PDB Ligand
D-cycloserine is an approved drug
Compound class: Synthetic organic
Comment: An analogue of the amino acid D-alanine and a component of the racemic drug with the INN cycloserine (D/L-cycloserine).

D-cycloserine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 64.35
Molecular weight 102.04
XLogP -0.92
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC1CONC1=O
Isomeric SMILES N[C@@H]1CONC1=O
InChI InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
InChI Key DYDCUQKUCUHJBH-UWTATZPHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(4R)-4-amino-1,2-oxazolidin-3-one
International Nonproprietary Names Click here for help
INN number INN
577 cycloserine
Synonyms Click here for help
Seromycin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cycloserine
Other databases
ChEMBL Ligand CHEMBL771
DrugBank Ligand DB00260
DrugCentral Ligand 759
GtoPdb PubChem SID 329968429
LIPID MAPS LMPK14000007
PubChem CID 6234
RCSB PDB Ligand 4AX
Search Google for chemical match using the InChIKey DYDCUQKUCUHJBH-UWTATZPHSA-N
Search Google for chemicals with the same backbone DYDCUQKUCUHJBH
Search PubMed clinical trials cycloserine
Search PubMed titles cycloserine
Search PubMed titles/abstracts cycloserine
UniChem Compound Search for chemical match using the InChIKey DYDCUQKUCUHJBH-UWTATZPHSA-N
UniChem Connectivity Search for chemical match using the InChIKey DYDCUQKUCUHJBH-UWTATZPHSA-N

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MedChemExpress
D-Cycloserine (links to external site)
Cat. No. HY-B0030