AntibioticMech

D-cycloserine

CHEBI:40009 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

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

Classification

cycloserine-like antibioticARO:3007154

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:23503 CHEBI:23503
• CHEBI:25558 CHEBI:25558
• CHEBI:25807 CHEBI:25807
• ARO:3007154 ARO:3007154

Chemical structure

Computed structure properties

Molecular formula	C3H6N2O2
Charge	0
Average mass	102.093 Da
Monoisotopic mass	102.04293 Da
Source	ChEBI
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

Also called

• Seromycin (BRAND_NAME)— chebi
• cicloserina (INN)— chebi
• cycloserine (INN)— chebi
• cycloserinum (INN)— chebi
• cyclosérine (INN)— chebi
• (4R)-4-aminoisoxazolidin-3-one (EXACT_SYNONYM)— chebi
• (+)-4-amino-3-isoxazolidinone (EXACT_SYNONYM)— chebi
• (+)-cycloserine (EXACT_SYNONYM)— chebi
• (R)-4-AMINO-ISOXAZOLIDIN-3-ONE (EXACT_SYNONYM)— chebi
• D-(+)-cycloserine (EXACT_SYNONYM)— chebi
• D-4-amino-3-isoxazolidinone (EXACT_SYNONYM)— chebi
• D-4-amino-3-isoxazolidone (EXACT_SYNONYM)— chebi
• D-Cycloserine (EXACT_SYNONYM)— chebi
• DCS (EXACT_SYNONYM)— chebi
• PA 94 (EXACT_SYNONYM)— chebi
• PA-94 (EXACT_SYNONYM)— chebi
• Ro-1-9213 (EXACT_SYNONYM)— chebi
• cyclo-D-serine (EXACT_SYNONYM)— chebi
• orientomycin (EXACT_SYNONYM)— chebi
• α-Cycloserine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3000760
• cas:68-41-7
• drugbank:DB00260
• drugcentral:759
• hmdb:HMDB0014405
• kegg.drug:D00877
• lincs.smallmolecule:LSM-5932
• lipidmaps:LMPK14000007
• metacyc.compound:CPD-2482
• patent:US2772280
• patent:US2840565
• pdb-ccd:4AX
• reaxys:80798
• wikipedia.en:Cycloserine
• chembl:CHEMBL771
• pubchem.compound:6234

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• CHEBI:33231 CHEBI:33231
• CHEBI:33281 CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record

Source	Native ID	Label	Minted CURIE	Version
ARO	ARO:3000760	cycloserine	antibioticmech:aro-000a78a459	2026-08-30
CHEBI	CHEBI:40009	D-cycloserine	antibioticmech:chebi-0c70ed4cf2	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

cycloserine sensitive alr PROTEIN DIRECT_BINDING_TARGET

ARO:3000722

CARD/ARO database assertion; target organism, strain, and assay are not specified. Alanine racemase is asserted as the cycloserine-sensitive enzyme. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3000722 (CARD/ARO asserts targeted_by_antibiotic ARO:3000760 (cycloserine); database assertion, not a primary citation.)

cycloserine sensitive D-alanine synthetase PROTEIN DIRECT_BINDING_TARGET

ARO:3000723

CARD/ARO database assertion; target organism, strain, and assay are not specified. D-alanine ligase is asserted as the cycloserine-sensitive enzyme. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3000723 (CARD/ARO asserts targeted_by_antibiotic ARO:3000760 (cycloserine); database assertion, not a primary citation.)

Mechanism summary

Clinical status

APPROVED

Resistance mechanisms

3 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 3

ANTIBIOTIC_TARGET_ALTERATION

Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium tuberculosis ald mutations confer resistance to cycloserine	ARO:3004945	not organism-specific	—	ARO:3004945 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000760 (cycloserine); database assertion, not a primary citation.)
Mycobacterium tuberculosis alr with mutation conferring resistance to cycloserine	ARO:3004947	not organism-specific	—	ARO:3004947 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000760 (cycloserine); database assertion, not a primary citation.)
Mycobacterium tuberculosis ddlA mutations confer resistance to cycloserine	ARO:3004941	not organism-specific	—	ARO:3004941 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000760 (cycloserine); database assertion, not a primary citation.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.