Chemical substance record

D-cycloserine

68-41-7C₃H₆N₂O₂102.093 g/mol

Organic/Inorganic Small MoleculeChEBI source record

A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine—D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	68-41-7	ChEBI ↗
Molecular formula	C₃H₆N₂O₂	ChEBI ↗
Molar mass	102.093 g/mol	ChEBI ↗
Monoisotopic mass	102.04293 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:40009	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	102.09 g/mol	PubChem ↗
Exact mass	102.042927438 Da	PubChem ↗
Computed XLogP	-1.5	PubChem ↗
Topological polar surface area (Å²)	64.4	PubChem ↗
H-bond donors	2	PubChem ↗
H-bond acceptors	3	PubChem ↗
Rotatable bonds	0	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

D-cycloserine

IUPAC name

(4R)-4-aminoisoxazolidin-3-one

InChIKey

DYDCUQKUCUHJBH-UWTATZPHSA-N

SMILES

[H][C@@]1(N)CONC1=O

InChI

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

Names & synonyms

(4R)-4-aminoisoxazolidin-3-onecicloserinacycloserinecycloserinumSeromycin

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

4-amino-1,2-oxazolidin-3-oneChEBI parent class · 23503 ↗organonitrogen heterocyclic antibioticChEBI parent class · 25558 ↗organooxygen heterocyclic antibioticChEBI parent class · 25807 ↗

organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

metaboliteantitubercular agentantimetaboliteantiinfective agentNMDA receptor agonist

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00979499 mol

Uses 102.093 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 3 atoms

35.29%

O

Oxygen · 2 atoms

31.34%

N

Nitrogen · 2 atoms

27.44%

H

Hydrogen · 6 atoms

5.92%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

D-cycloserine for Alzheimer's disease. ↗The Cochrane database of systematic reviews · 2002 · PMID 12076471

Learning and memory in conditioned fear extinction: effects of D-cycloserine. ↗Acta psychologica · 2008 Mar · PMID 17707326

US2772280 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US2840565 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:40009

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 6234 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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