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).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 CDK toolkit. 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
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.

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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
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, seromycin, orientomycin, oxamycin, tisomycin
Other databases
ChEMBL Ligand CHEMBL771
DrugBank Ligand DB00260
DrugCentral Ligand 759
GtoPdb PubChem SID 329968429
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